(3R)-1,3-decanediol -Drug Synthesis Database

【结构式】

【分子编号】59084

【品名】(3R)-1,3-decanediol

【CA登记号】

【分子式】C₁₀H₂₂O₂

【分子量】174.28348

【元素组成】C 68.92% H 12.72% O 18.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XVI)

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).

参考文献中间体

合成目标

【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：(III)

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).

参考文献中间体

合成目标

【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	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