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CAS 551-16-6
(+)-6-Aminopenicillanic acid
登记编号：Amoxicillin-013、Tazobactam Sodium-021
应用背景（按来源药适应症）
幽门螺杆菌感染阿莫西林/奥美拉唑/利福布汀消化不良阿莫西林/奥美拉唑/利福布汀腹腔感染他唑巴坦钠/头孢洛生呼吸机相关性肺炎他唑巴坦钠/头孢洛生泌尿系统感染他唑巴坦钠/头孢洛生社区获得性细菌肺炎他唑巴坦钠/头孢洛生肾盂肾炎他唑巴坦钠/头孢洛生医院获得性肺炎他唑巴坦钠/头孢洛生十二指肠溃疡雷贝拉唑钠/甲硝唑/阿莫西林特发性血小板减少性紫癜雷贝拉唑钠/甲硝唑/阿莫西林胃溃疡雷贝拉唑钠/甲硝唑/阿莫西林胃炎雷贝拉唑钠/甲硝唑/阿莫西林幽门螺杆菌感染雷贝拉唑钠/甲硝唑/阿莫西林边缘带B细胞淋巴瘤克拉霉素/雷贝拉唑钠/阿莫西林十二指肠溃疡克拉霉素/雷贝拉唑钠/阿莫西林特发性血小板减少性紫癜克拉霉素/雷贝拉唑钠/阿莫西林胃溃疡克拉霉素/雷贝拉唑钠/阿莫西林胃炎克拉霉素/雷贝拉唑钠/阿莫西林幽门螺杆菌感染克拉霉素/雷贝拉唑钠/阿莫西林细菌感染头孢他啶/他唑巴坦钠呼吸道感染头孢他啶/他唑巴坦钠泌尿系统感染头孢他啶/他唑巴坦钠
来源药（使用该中间体的合成路线）
| 品种 | 梯队 | 到期年 |
|---|---|---|
| 阿莫西林/奥美拉唑/利福布汀Amoxicillin/Omeprazole/Rifabutin | Tier C · 观察 / 贸易 | - |
| 他唑巴坦钠/头孢洛生Tazobactam Sodium/Ceftolozane | Tier C · 观察 / 贸易 | - |
| 雷贝拉唑钠/甲硝唑/阿莫西林Rabeprazole Sodium/Metronidazole/Amoxicillin | Tier C · 观察 / 贸易 | - |
| 克拉霉素/雷贝拉唑钠/阿莫西林Clarithromycin/Rabeprazole Sodium/Amoxicillin | Tier C · 观察 / 贸易 | - |
| 头孢他啶/他唑巴坦钠Ceftazidime/Tazobactam Sodium | Tier C · 观察 / 贸易 | - |
合成路线中的位置（上下游链）
按路线登记顺序排列，左→右为合成方向；高亮为当前 CAS，其余可点击跳转对应档案。
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Methyl (2S,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-(Trimethylsilyl)-1,2,3-triazole→1,2,3-Triazole→3-(1,2,3-Triazol-4-yl)pyridine→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester→Methyl (2S,3S,5R)-3-methyl-7-oxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→Benzhydryl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→Methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(Diphenylmethylidene)hydrazine→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Diphenylmethyl (2S,4R,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[(tert-Butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R,6R)-6-[(tert-butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Methyl glyoxylate→(S)-(-)-1-Phenylethylamine→(1S)-1-(2-Naphthyl)ethanamine→Methyl (2Z)-[[(1S)-1-phenylethyl]imino]acetate→Methyl (2Z)-[[(1S)-1-(naphthalen-2-yl)ethyl]imino]acetate→Carbolic acid→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate→Methyl (2R)-(4-hydroxyphenyl)[(1-phenylethyl)amino]acetate hydrogen chloride (1/1)→Methyl (2R)-(4-hydroxyphenyl)[[1-(naphthalen-2-yl)ethyl]amino]acetate hydrogen chloride (1/1)→D-p-Hydroxyphenylglycine methyl ester hydrochloride→D-p-yHdroxyphenylglycine methyl ester→(+)-6-Aminopenicillanic acid
[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-[[(Benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[(2R)-2-[[(benzyloxy)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→1-Methoxybutane-1,3-dione→Sodium (2R)-(4-hydroxyphenyl)[[(2E)-4-methoxy-4-oxobut-2-en-2-yl]amino]acetate→Sodium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Potassium (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(+)-6-Aminopenicillanic acid
(2R)-[[(Benzyloxy)carbonyl]amino](4-hydroxyphenyl)acetic acid→(2R)-[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-Amino(4-hydroxyphenyl)acetyl chloride hydrogen chloride
[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[[[(Benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Sodium (2S,5R,6R)-6-[[[[(benzyloxy)carbonyl]amino](4-[[(benzyloxy)carbonyl]oxy]phenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid→(2R)-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)(4-hydroxyphenyl)acetic acid→(+)-6-Aminopenicillanic acid→(2S,5R,6R)-6-[[(2R)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R)-6,6-Dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Methyl (2S,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-(Trimethylsilyl)-1,2,3-triazole→1,2,3-Triazole→3-(1,2,3-Triazol-4-yl)pyridine→(2S,3S,5R)-2-Methyl-2-(1H-1,2,3-triazol-1-ylmethyl)penam-3-carboxylic acid diphenylmethyl ester→Methyl (2S,3S,5R)-3-methyl-7-oxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→Benzhydryl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→Methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Diphenylmethyl (2S,3R,5R)-3-(bromomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(Diphenylmethylidene)hydrazine→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→Diphenylmethyl (2S,4R,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R,6R)-6-[(tert-Butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→Diphenylmethyl (2S,5R,6R)-6-[(tert-butoxycarbonyl)amino]-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
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