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【结 构 式】

【分子编号】59096

【品名】(1R)-1-(2-{[(2S,3R,4R,5S,6R)-3-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate

【CA登记号】

【 分 子 式 】C34H65N3O7Si

【 分 子 量 】655.99162

【元素组成】C 62.25% H 9.99% N 6.41% O 17.07% Si 4.28%

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:(XXXI)

The common precursor (XVIII) was converted into building block (XXXV) as follows. Esterification of (XVIII) with the unsaturated fatty acid (XXIX) by means of DCC and DMAP gave ester (XXX). The acetonide group of (XXX) was then hydrolyzed to diol (XXXI) under acidic conditions. Methylation of (XXXI) with iodomethane in the presence of silver oxide produced a mixture of two regioisomeric methyl ethers. In this mixture, the undesired 4-methoxy compound (XXXIII) was then selectively silylated at the free primary 6-hydroxyl group, which allowed chromatographic separation from the target 6-methoxy compound (XXXII). Phosphitylation of (XXXII), followed by oxidation of the intermediate phosphite with m-chloroperbenzoic acid, furnished phosphate (XXXIV). Desilylation of (XXXIV) to the required intermediate (XXXV) was accomplished by treatment with HF in acetonitrile.

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
(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
(XXIX) 49124 (Z)-5-dodecenoic acid C12H22O2 详情 详情
(XXX) 59095 (1R)-1-{2-[((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]ethyl}octyl (Z)-5-dodecenoate C37H69N3O7Si 详情 详情
(XXXI) 59096 (1R)-1-(2-{[(2S,3R,4R,5S,6R)-3-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate C34H65N3O7Si 详情 详情
(XXXII) 59097 (1R)-1-(2-{[(2S,3R,4R,5S,6R)-3-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-6-(methoxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate C35H67N3O7Si 详情 详情
(XXXIII) 59098 (1R)-1-(2-{[(2S,3R,4R,5S,6R)-3-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-methoxytetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate C51H85N3O7Si2 详情 详情
(XXXIV) 59099 (1R)-1-(2-{[(2S,3R,4R,5S,6R)-3-azido-5-{[bis(allyloxy)phosphoryl]oxy}-2-{[tert-butyl(dimethyl)silyl]oxy}-6-(methoxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate C41H76N3O10PSi 详情 详情
(XXXV) 59100 (1R)-1-(2-{[(3R,4R,5S,6R)-3-azido-5-{[bis(allyloxy)phosphoryl]oxy}-2-hydroxy-6-(methoxymethyl)tetrahydro-2H-pyran-4-yl]oxy}ethyl)octyl (Z)-5-dodecenoate C35H62N3O10P 详情 详情
Extended Information