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【结 构 式】

【分子编号】57275

【品名】(3S,4S,5S,7S,8R,12S,14S,15R,16S,18R,26aS)-8-allyl-15-{[tert-butyl(dimethyl)silyl]oxy}-20-[(2,4-dimethoxybenzyl)oxy]-14,16-dimethoxy-7-[(4-methoxybenzyl)oxy]-3-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-4,10,12,18-tetramethyl-19-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,19,20,24,25,26,26a-octadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,21(4H,23H)-dione

【CA登记号】

【 分 子 式 】C91H161NO15Si4

【 分 子 量 】1621.61908

【元素组成】C 67.4% H 10.01% N 0.86% O 14.8% Si 6.93%

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:(LII)

The condensation of carbaldehyde (XLVIII) with the chiral intermediate phosphonamide (XXXII), by means of BuLi, gives the adduct (XLIX), which is treated with phenyliodonium trifluoroacetate and AcOH to cleave the 1,3-dithiane ring and yield the carbaldehyde (L). The cyclocondensation of (L) with 2-(2,4-dimethoxybenzyloxy)acetic acid methyl ester (LI) by means of LDA, LiOH, TesOTf and 2-chloro-1-methylpyridinium iodide (CMPI) affords the macrolactone (LII), which is submitted to a sequence of deprotection (DDQ), oxidation (DMP), deprotection (TFA) and oxidation (DMP) to provide the tricarbonyl compound (LIII). A similar sequence (TFA, DMP, DDQ, and DMP) can also be used to obtain the tricarbonyl compound (LIII). Finally this compound is fully desilylated by means of HF in acetonitrile to provide the target FK-506.

1 Ragan, J.A.; The total synthesis of FK506 and an FKBP probe reagent, (C8,C9-13C2)-FK506. Diss Abstr Int B - Sci Eng 1991, 51, 8, 3849.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXII) 11491 (3R,5S,6R,7S,9R)-6-[[tert-Butyl(dimethyl)silyl]oxy]-9-(1,3-dithian-2-yl)-5,7-dimethoxy-1,3-dimethyldecyl-N,N,N',N'-tetramethylphosphonic diamide C28H61N2O4PS2Si 详情 详情
(XLVIII) 57271 1-(tert-butyl) 2-{(1S,2S,3S,5S,6S)-6-formyl-5-[(4-methoxybenzyl)oxy]-1-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-2-methyl-3-[(triisopropylsilyl)oxy]-8-nonenyl} (2S)-1,2-piperidinedicarboxylate C58H101NO10Si2 详情 详情
(XLIX) 57272 2-{(1S,2S,3S,5S,6R,7E,10S,12S,13R,14S,16R)-6-allyl-13-{[tert-butyl(dimethyl)silyl]oxy}-16-(1,3-dithian-2-yl)-12,14-dimethoxy-5-[(4-methoxybenzyl)oxy]-1-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-2,8,10-trimet C82H149NO12S2Si3 详情 详情
(L) 57273 2-{(1S,2S,3S,5S,6R,7E,10S,12S,13R,14S,16R)-6-allyl-13-{[tert-butyl(dimethyl)silyl]oxy}-12,14-dimethoxy-5-[(4-methoxybenzyl)oxy]-1-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-2,8,10,16-tetramethyl-17-oxo-3-[(tr C79H143NO13Si3 详情 详情
(LI) 57274 methyl 2-[(2,4-dimethoxybenzyl)oxy]acetate C12H16O5 详情 详情
(LII) 57275 (3S,4S,5S,7S,8R,12S,14S,15R,16S,18R,26aS)-8-allyl-15-{[tert-butyl(dimethyl)silyl]oxy}-20-[(2,4-dimethoxybenzyl)oxy]-14,16-dimethoxy-7-[(4-methoxybenzyl)oxy]-3-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-4,10,12,18-tetramethyl-19-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,19,20,24,25,26,26a-octadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,21(4H,23H)-dione C91H161NO15Si4 详情 详情
(LIII) 11499 (3S,4S,5S,8R,12S,14S,15R,16S,18R,26aS)-8-Allyl-15-[[tert-butyl(dimethyl)silyl]oxy]-14,16-dimethoxy-3-((E)-2-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-1-methylethenyl)-4,10,12,18-tetramethyl-5-[(triisopropylsilyl)oxy]-5,6,11,12,13,14,15,16,17,18,24,25,26,26a-tetradecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,7,19,20,21(4H,8H,23H)-pentone C68H123NO12Si3 详情 详情
Extended Information