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【结 构 式】

【分子编号】42732

【品名】(3R,4S,5S,6S)-6-((2S,3Z,5S,6S,7S,8Z,11S,13R,14S,15S,16Z)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethyl-12-oxo-3,8,16,18-nonadecatetraenyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyltetrahydro-2H-pyran-2-one

【CA登记号】

【 分 子 式 】C50H94O7Si3

【 分 子 量 】891.54866

【元素组成】C 67.36% H 10.63% O 12.56% Si 9.45%

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:(LIII)

The target compound has been obtained as follows: The condensation of bromo derivative intermediate (XXXIII) with the ketone intermediate (XLIII) by means of LDA gives the adduct (L), which is methylated with methyl iodide and (Tbdps)2N-Li to yield the pentamethyl compound (LI). The desulfuration of (LI) by reaction with HgCl2 followed by oxidation with Jones reagent affords the tetrahydroyranone derivative (LII), which is debenzylated by means of DDQ to furnish the secondary alcohol (LIII). The reaction of (LIII) with trichloroacetyl isocyanate gives the carbamate (LIV), which is reduced with LiAlH(OBu)3I, yielding the secondary alcohol (LV). Finally, this compound is desilylated by treatment with HCl in methanol.

1 Hung, D.T.; et al.; Syntheses of discodermolides useful for investigating microtubule binding and stabilization. J Am Chem Soc 1996, 118, 45, 11054.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXIII) 42716 (5S,6Z,8S,9S)-9-[(1S,2Z)-4-bromo-1,3-dimethyl-2-butenyl]-5-[[(2S,3S,4S,5R,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyl-6-(phenylsulfanyl)tetrahydro-2H-pyran-2-yl]methyl]-2,2,3,3,8,11,11,12,12-nonamethyl-4,10-dioxa-3,11-disila-6-tridecene; (2S,3S,4S,5R,6S)-2-((2S,3Z,5S,6S,7S,8Z)-10-bromo-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5,7,9-trimethyl-3,8-decadienyl)-3,5-dimethyl-6-(phenylsulfanyl)tetrahydro-2H-pyran-4-yl tert-butyl(dimethyl)silyl ether n/a C44H81BrO4SSi3 详情 详情
(XLIII) 42722 (3R,4S,5S,6Z)-4-[(4-methoxybenzyl)oxy]-3,5-dimethyl-6,8-nonadien-2-one C19H26O3 详情 详情
(L) 42729 (3Z,5S,6S,7R,11Z,13S,14S,15S,16Z,18S)-14,18-bis[[tert-butyl(dimethyl)silyl]oxy]-19-[(2S,3S,4S,5R,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyl-6-(phenylsulfanyl)tetrahydro-2H-pyran-2-yl]-6-[(4-methoxybenzyl)oxy]-5,7,11,13,15-pentamethyl-1,3,11 C63H106O7SSi3 详情 详情
(LI) 42730 (3Z,5S,6S,7R,9S,11Z,13S,14S,15S,16Z,18S)-14,18-bis[[tert-butyl(dimethyl)silyl]oxy]-19-[(2S,3S,4S,5R,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyl-6-(phenylsulfanyl)tetrahydro-2H-pyran-2-yl]-6-[(4-methoxybenzyl)oxy]-5,7,9,11,13,15-hexamethyl-1, C64H108O7SSi3 详情 详情
(LII) 42731 (3R,4S,5S,6S)-6-[(2S,3Z,5S,6S,7S,8Z,11S,13R,14S,15S,16Z)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-14-[(4-methoxybenzyl)oxy]-5,7,9,11,13,15-hexamethyl-12-oxo-3,8,16,18-nonadecatetraenyl]-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyltetrahydro-2H-pyr C58H102O8Si3 详情 详情
(LIII) 42732 (3R,4S,5S,6S)-6-((2S,3Z,5S,6S,7S,8Z,11S,13R,14S,15S,16Z)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethyl-12-oxo-3,8,16,18-nonadecatetraenyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyltetrahydro-2H-pyran-2-one C50H94O7Si3 详情 详情
(LIV) 42733 (1S,2R,4S,6Z,8S,9S,10S,11Z,13S)-9,13-bis[[tert-butyl(dimethyl)silyl]oxy]-14-((2S,3S,4S,5R)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyl-6-oxotetrahydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-3-oxo-6,11-tetradec C51H95NO8Si3 详情 详情
(LV) 42734 (1S,2S,3R,4S,6Z,8S,9S,10S,11Z,13S)-9,13-bis[[tert-butyl(dimethyl)silyl]oxy]-14-((2S,3S,4S,5R)-4-[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyl-6-oxotetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4,6,8,10-pentamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-6,11-t C51H97NO8Si3 详情 详情
Extended Information