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【结 构 式】

【分子编号】59083

【品名】methyl (3R)-3-hydroxydecanoate

【CA登记号】

【 分 子 式 】C11H22O3

【 分 子 量 】202.29388

【元素组成】C 65.31% H 10.96% O 23.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XV)

Reformatskii condensation of the organozinc reagent derived from methyl bromoacetate (XIII) with n-heptyl cyanide (XII) gave rise to the keto ester adduct (XIV). Catalytic hydrogenation of (XIV) in the presence of the chiral catalyst generated from dichloro(cycloocta-1,5-diene)ruthenium and (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl furnished the (R)-hydroxyester (XV) in high enantiomeric excess. Ester group reduction in (XV) by means of LiAlH4 afforded diol (XVI), which was further converted to the primary tosylate (XVII) with p-toluenesulfonyl chloride in pyridine. Then, alkylation of the intermediate alcohol (XI) with tosylate (XVII) under Williamson's ether synthesis conditions provided the common precursor (XVIII).

1 Christ, W.J.; Kawata, T.; Hawkins, L.D.; Kobayashi, S.; Asano, O.; Rossignol, D.P. (Eisai Co., Ltd.); Anti-endotoxin cpds.. EP 0536969; JP 1993194470; US 5530113 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 59080 (4aR,6S,7R,8R,8aS)-7-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-ol C15H29N3O5Si 详情 详情
(XII) 59081 octanenitrile 124-12-9 C8H15N 详情 详情
(XIII) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(XIV) 59082 methyl 3-oxodecanoate C11H20O3 详情 详情
(XV) 59083 methyl (3R)-3-hydroxydecanoate C11H22O3 详情 详情
(XVI) 59084 (3R)-1,3-decanediol C10H22O2 详情 详情
(XVII) 49121 (3R)-3-hydroxydecyl 4-methylbenzenesulfonate C17H28O4S 详情 详情
(XVIII) 59085 (3R)-1-[((4aR,6S,7R,8R,8aS)-7-azido-6-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy]-3-decanol C25H49N3O6Si 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

Saponification of (R)-methyl 3-hydroxydecanoate (I) gave hydroxy acid (II), which was reduced to diol (III) using LiAlH4. Selective sulfonylation of the primary hydroxyl group of (III) provided tosylate (IV). The secondary hydroxyl group of (IV) was subsequently alkylated with iodomethane in the presence of NaH to furnish the methyl ether (V).

1 Kobayashi, S.; Kawata, T.; Christ, W.J.; Rossignol, D.P. (Eisai Co., Ltd.); Substd. liposaccharides useful in the treatment and prevention of endotoxemia. US 5750664; WO 9639411 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 59083 methyl (3R)-3-hydroxydecanoate C11H22O3 详情 详情
(II) 64140 (3R)-3-hydroxydecanoic acid C10H20O3 详情 详情
(III) 59084 (3R)-1,3-decanediol C10H22O2 详情 详情
(IV) 49121 (3R)-3-hydroxydecyl 4-methylbenzenesulfonate C17H28O4S 详情 详情
(V) 64141 (3R)-3-methoxydecyl 4-methylbenzenesulfonate C18H30O4S 详情 详情
Extended Information