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CAS 139689-03-5

((2R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxathiolan-2-yl)methanol

Codes:EMTR-015

Application context (from source-drug indications)

HIV感染比克恩丙诺乙型肝炎比克恩丙诺HIV感染恩曲他滨/富马酸磷丙替诺福韦获得性免疫缺损综合征恩曲他滨/富马酸磷丙替诺福韦进行性多病灶脑白质病恩曲他滨/富马酸磷丙替诺福韦HIV感染恩曲他滨/盐酸利匹韦林/富马酸替诺福韦二吡呋酯

Source drugs (routes using this intermediate)

DrugTierExpiry
比克恩丙诺Bictegravir/Emtricitabine/Tenofovir Alafenamide FumarateTier B — Position early-
恩曲他滨/富马酸磷丙替诺福韦Emtricitabine/Tenofovir Alafenamide FumarateTier B — Position early-
恩曲他滨/盐酸利匹韦林/富马酸替诺福韦二吡呋酯Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateTier B — Position early-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

比克恩丙诺优化路线steps: 10total yield: 5.5 mg
(2S,3S,4S,5S,6S)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol→(2R,3S,4S,5R,6S)-6-((tosyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate→(2R,3S,4S,5R,6S)-2-bromo-6-((tosyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate→potassium O-ethyl carbonodithioate→(2S,3S,4S)-8-oxa-6-thiabicyclo[3.2.1]octane-2,3,4-triol→((2R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxathiolan-2-yl)methanol→(R)-1-((2R,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)ethane-1,2-diol→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolane-5-carboxylic acid→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl acetate→N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→N-(1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide→4-amino-1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one
恩曲他滨/富马酸磷丙替诺福韦优化路线steps: 10total yield: 5.5 mg
(2S,3S,4S,5S,6S)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol→(2R,3S,4S,5R,6S)-6-((tosyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate→(2R,3S,4S,5R,6S)-2-bromo-6-((tosyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate→potassium O-ethyl carbonodithioate→(2S,3S,4S)-8-oxa-6-thiabicyclo[3.2.1]octane-2,3,4-triol→((2R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxathiolan-2-yl)methanol→(R)-1-((2R,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)ethane-1,2-diol→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolane-5-carboxylic acid→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl acetate→N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→N-(1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide→4-amino-1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one
(2S,3S,4S,5S,6S)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol→(2R,3S,4S,5R,6S)-6-((tosyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate→(2R,3S,4S,5R,6S)-2-bromo-6-((tosyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate→potassium O-ethyl carbonodithioate→(2S,3S,4S)-8-oxa-6-thiabicyclo[3.2.1]octane-2,3,4-triol→((2R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxathiolan-2-yl)methanol→(R)-1-((2R,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)ethane-1,2-diol→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolane-5-carboxylic acid→(2R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl acetate→N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→N-(1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide→4-amino-1-((2R,5S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one

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