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CAS 1513876-42-0

tert-butyl(((1E,3S)-1-((3aR,4R,6aS)-2-methoxy-5-(((trimethylsilyl)oxy)methylene)hexahydro-2H-cyclopenta[b]furan-4-yl)-5-phenylpent-1-en-3-yl)oxy)dimethylsilane

Codes: BIMA-058

Application context (from source-drug indications)

Ocular hypertensionBimatoprost/Timolol MaleateOpen-angle glaucomaBimatoprost/Timolol MaleateGlaucomaBimatoprost/Timolol MaleateOcular hypertensionBimatoprostGlaucomaBimatoprost少毛症BimatoprostOpen-angle glaucomaBimatoprost白内障Bimatoprost瘢痕Bimatoprost

Source drugs (routes using this intermediate)

DrugTierExpiry
Bimatoprost/Timolol MaleateTier C — Watch / trade-
BimatoprostTier 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.

Bimatoprost/Timolol MaleateOptimised routesteps: 11total yield: 82.6 mg
(3aR,4R,5R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol→3-phenylpropanal→2,5-dimethoxytetrahydrofuran→(3aR,6aS)-2-hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde→(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde→(S,E)-tert-butyl((1-iodo-5-phenylpent-1-en-3-yl)oxy)dimethylsilane→tert-butyl(((1E,3S)-1-((3aR,4R,6aS)-2-methoxy-5-(((trimethylsilyl)oxy)methylene)hexahydro-2H-cyclopenta[b]furan-4-yl)-5-phenylpent-1-en-3-yl)oxy)dimethylsilane→(3aR,4R,5R,6aS)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol→(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide→2-methylbut-3-yn-2-ol→(S)-5-((tert-butyldimethylsilyl)oxy)-2-methyl-7-phenylhept-3-yn-2-ol→(S)-tert-butyldimethyl((5-phenylpent-1-yn-3-yl)oxy)silane→5-bromopentanoic acid→5-bromo-N-ethylpentanamide
BimatoprostOptimised routesteps: 11total yield: 82.6 mg
(3aR,4R,5R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol→3-phenylpropanal→2,5-dimethoxytetrahydrofuran→(3aR,6aS)-2-hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde→(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde→(S,E)-tert-butyl((1-iodo-5-phenylpent-1-en-3-yl)oxy)dimethylsilane→tert-butyl(((1E,3S)-1-((3aR,4R,6aS)-2-methoxy-5-(((trimethylsilyl)oxy)methylene)hexahydro-2H-cyclopenta[b]furan-4-yl)-5-phenylpent-1-en-3-yl)oxy)dimethylsilane→(3aR,4R,5R,6aS)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol→(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide→2-methylbut-3-yn-2-ol→(S)-5-((tert-butyldimethylsilyl)oxy)-2-methyl-7-phenylhept-3-yn-2-ol→(S)-tert-butyldimethyl((5-phenylpent-1-yn-3-yl)oxy)silane→5-bromopentanoic acid→5-bromo-N-ethylpentanamide

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