(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 -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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