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【结 构 式】

【分子编号】39184

【品名】methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-(hydroxymethyl)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate

【CA登记号】

【 分 子 式 】C22H36O7

【 分 子 量 】412.52364

【元素组成】C 64.05% H 8.8% O 27.15%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVII)

The hydrolysis of 2-oxa-3-oxo-6-syn-hydroxymethyl-7-anti-acetoxy-cis-bicyclo[3.3.0]octane (VIII) (2) with KOH in methanol gives the dihydroxy compound (IX), which is acetylated with acetic anhydride in pyridine to give the acetoxymethyl compound (X). The treatment of (X) with dihydropyran and p-toluenesulfonic acid in methylene chloride affords the tetrahydropyranyl derivative (XI), which is reduced with diisobutylaluminum hydride in toluene to yield 2-oxa-3-hydroxy-6-syn-hydroxymethyl-7-anti-(2-tetrahydropyranyloxy)-cis-bicyclo[3.3.0]octane (XII). The Wittig reaction of (XII) with 4-carboxybutyltriphenylphosphonium bromide (B) by means of NaH in DMSO gives 2alpha-(6-carboxyhex-2-cis-enyl)-3beta-hydroxymethyl-4alpha-(2-tetrahydropyranyloxy)cyclopentan-1alpha-ol (XIII), which is esterified with CH2N2 to the corresponding methyl ester (XIV). The reaction of (XIV) with trimethylchlorosilane in pyridine - methylene chloride gives the monotrimethylsilyl derivative (XV), which is acetylated with acetyl chloride affording the fully protected compound (XVI). The partial hydrolysis of (XVI) with oxalic acid in water-ethyl acetate yields the compound (XVII) with a free hydroxymethyl group, which is finally oxidized with CrO3 in methylene chloride pyridine to give the starting 1alpha-acetoxy-2alpha-(6-methoxycarbonylhex-2-cis-enyl)-3beta-formyl-4alpha-(2-tetrahydropyranyloxy)cyclopentane (I).

1 Hayashi, M.; et al.; US 4065632 .
2 Castaner, J.; Riberos, J.; ONO-995. Drugs Fut 1980, 5, 10, 499.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIIa) 39177 (2R,3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-ol C14H24O5 详情 详情
(XIIb) 39178 (2S,3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-ol C14H24O5 详情 详情
(B) 39179 butyl(triphenyl)phosphonium bromide 1779-51-7 C22H24BrP 详情 详情
(I) 39185 ethyl 2-[3-(trifluoromethyl)phenoxy]acetate C11H11F3O3 详情 详情
(VIII) 39173 (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl acetate C10H14O5 详情 详情
(IX) 39174 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 32233-40-2 C8H12O4 详情 详情
(X) 39175 [(3aR,4S,5R,6aS)-5-hydroxy-2-oxohexahydro-2H-cyclopenta[b]furan-4-yl]methyl acetate C10H14O5 详情 详情
(XI) 39176 [(3aR,4S,5R,6aS)-2-oxo-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexahydro-2H-cyclopenta[b]furan-4-yl]methyl acetate C16H24O6 详情 详情
(XIII) 39180 (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-(hydroxymethyl)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoic acid C19H32O6 详情 详情
(XIV) 39181 methyl (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-(hydroxymethyl)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate C20H34O6 详情 详情
(XV) 39182 methyl (Z)-7-((1R,2S,3R,5S)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[[(trimethylsilyl)oxy]methyl]cyclopentyl)-5-heptenoate C23H42O6Si 详情 详情
(XVI) 39183 methyl (Z)-7-((1R,2S,3R,5S)-5-(acetoxy)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[[(trimethylsilyl)oxy]methyl]cyclopentyl)-5-heptenoate C25H44O7Si 详情 详情
(XVII) 39184 methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-(hydroxymethyl)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate C22H36O7 详情 详情
Extended Information