(3R,4S,5R,6S)-4-methoxy-3,5-dimethyl-6-((2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-tris[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethyl-3,8,16,18-nonadecatetraenyl)tetrahydro-2H-pyran-2-one -Drug Synthesis Database

【结构式】

【分子编号】42686

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

【CA登记号】

【分子式】C₅₁H₉₈O₇Si₃

【分子量】907.59142

【元素组成】C 67.49% H 10.88% O 12.34% Si 9.28%

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：(XXXVI)

The condensation of (XXXIV) with the intermediate aldehyde (XXV) by means of NaHMDS gives the fully protected lactone derivative (XXXV), which is selectively deprotected at the Pmb group with DDQ, yielding the secondary alcohol (XXXVI). The reaction of (XXXVI) with trichloroacetyl isocyanate and Al2O3 affords the corresponding carbamate (XXXVII), which is finally desilylated with HCl in methanol.

参考文献中间体

合成目标

【1】 Smith, A.B. III; et al.; Evolution of a gram-scale synthesis of (+)-discodermolide. J Am Chem Soc 2000, 122, 36, 8654.
【2】 Smith, A.B. III; et al.; Gram-scale synthesis of (+)-discodermolide. Org Lett 1999, 1, 11, 1823.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXV)	42675	(2S)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-[(2S,3R,4S,5R)-4-methoxy-3,5-dimethyl-6-oxotetrahydro-2H-pyran-2-yl]propanal	C₁₇H₃₂O₅Si	详情	详情
(XXXIV)	42684	[(2R,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[(4-methoxybenzyl)oxy]-2,4,6,8,10,12-hexamethyl-5,13,15-hexadecatrienyl](triphenyl)phosphonium iodide	C₆₀H₉₀IO₄PSi₂	详情	详情
(XXXV)	42685	(3R,4S,5R,6S)-4-methoxy-3,5-dimethyl-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-tris[[tert-butyl(dimethyl)silyl]oxy]-14-[(4-methoxybenzyl)oxy]-5,7,9,11,13,15-hexamethyl-3,8,16,18-nonadecatetraenyl]tetrahydro-2H-pyran-2-one	C₅₉H₁₀₆O₈Si₃	详情	详情
(XXXVI)	42686	(3R,4S,5R,6S)-4-methoxy-3,5-dimethyl-6-((2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-tris[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethyl-3,8,16,18-nonadecatetraenyl)tetrahydro-2H-pyran-2-one	C₅₁H₉₈O₇Si₃	详情	详情
(XXXVII)	42687	(1S,2R,3R,4S,6Z,8S,9S,10S,11Z,13S)-3,9,13-tris[[tert-butyl(dimethyl)silyl]oxy]-14-[(2S,3R,4S,5R)-4-methoxy-3,5-dimethyl-6-oxotetrahydro-2H-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-[(1S,2Z)-1-methyl-2,4-pentadienyl]-6,11-tetradecadienyl carbamate	C₅₂H₉₉NO₈Si₃	详情	详情

Extended Information