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CAS 31752-99-5

(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

CodesTAFL-020、LUBI-016

Application context (from source-drug indications)

高眼压他氟前列素开角型青光眼他氟前列素青光眼他氟前列素便秘芦比前列酮阿片类药物引起的便秘芦比前列酮慢性特发性便秘芦比前列酮药物相关的副作用和不良反应芦比前列酮非酒精性脂肪性肝炎芦比前列酮腹膜癌芦比前列酮

Source drugs (routes using this intermediate)

DrugTierExpiry
他氟前列素TafluprostTier C — Watch / trade-
芦比前列酮LubiprostoneTier C — Watch / trade-

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.

他氟前列素优化路线steps: 14total yield: 1.5 g
(4-carboxybutyl)triphenylphosphonium bromidetert-butyl 5-formylpyrazine-2-carboxylate(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one(3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one(3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol(Z)-7-((1R,2S,3R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acidisopropyl (Z)-7-((1R,2S,3R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoateisopropyl (Z)-7-((1R,2S,3R,5S)-5-acetoxy-2-(((tert-butyldimethylsilyl)oxy)methyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoateisopropyl (Z)-7-((1R,2S,3R,5S)-5-acetoxy-2-(hydroxymethyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoateisopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoatedimethyl (2-oxo-3-phenoxypropyl)phosphonateisopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoateisopropyl (Z)-7-((1R,2R,3R,5S)-5-acetoxy-3-hydroxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)cyclopentyl)hept-5-enoate(1R,3S,4R,5R)-4-((Z)-7-isopropoxy-7-oxohept-2-en-1-yl)-5-((E)-3-oxo-4-phenoxybut-1-en-1-yl)cyclopentane-1,3-diyl diacetate(1S,3R,4R,5R)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-((Z)-7-isopropoxy-7-oxohept-2-en-1-yl)cyclopentane-1,3-diyl diacetate
芦比前列酮优化路线steps: 11total yield: /
dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate(Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acid(3aR,4S,5R,6aS)-2-oxo-4-(((trimethylsilyl)oxy)methyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate(3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one(3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol(6-methoxy-6-oxohexyl)triphenylphosphonium bromidemethyl (Z)-7-((1R,2R,3R,5S)-2-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoatemethyl (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate

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