(1,1-dimethylethyl)(dimethyl)silyl 14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl ether; (1,1-dimethylethyl){[14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl]oxy}dimethylsilane -Drug Synthesis Database

【结构式】

【分子编号】64753

【品名】(1,1-dimethylethyl)(dimethyl)silyl 14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl ether; (1,1-dimethylethyl){[14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl]oxy}dimethylsilane

【CA登记号】

【分子式】C₅₅H₈₈O₉Si

【分子量】921.38382

【元素组成】C 71.7% H 9.63% O 15.63% Si 3.05%

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：(XXVII)

Wittig condensation of aldehyde (XXV) with the phosphonium salt (XXVI) produces the olefin adduct (XXVII). The O-silyl protecting group of (XXVII) is then removed by treatment with tetrabutylammonium fluoride to afford alcohol (XXVIII).

参考文献中间体

合成目标

【1】 Choy, N.; Shin, Y.; Nguyen, P.Q.; Curran, D.P.; Balachandran, R.; Madiraju, C.; Day, B.W.; Simplified discodermolide analogues: Synthesis and biological evaluation of 4-epi-7-dehydroxy-14,16-didemethyl-(+)-discodermolides as microtubule-stabilizing agents. J Med Chem 2003, 46, 14, 2846.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXV)	64751	8-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,4-dimethyl-3-({[4-(methyloxy)phenyl]methyl}oxy)-5-octenal	C₂₈H₄₄O₇	详情	详情
(XXVI)	64752	[6-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5,7-dimethyl-4-({[4-(methyloxy)phenyl]methyl}oxy)-8,10-undecadienyl](triphenyl)phosphonium iodide	C₄₅H₆₀IO₃PSi	详情	详情
(XXVII)	64753	(1,1-dimethylethyl)(dimethyl)silyl 14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl ether; (1,1-dimethylethyl){[14-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-2,8,10-trimethyl-3,9-bis({[4-(methyloxy)phenyl]methyl}oxy)-1-(1-methyl-2,4-pentadienyl)-6,11-tetradecadienyl]oxy}dimethylsilane	C₅₅H₈₈O₉Si	详情	详情
(XXVIII)	64754	19-(3,5-dimethyl-6-(methyloxy)-4-{[(methyloxy)methyl]oxy}tetrahydro-2H-pyran-2-yl)-5,7,13,15-tetramethyl-8,14-bis({[4-(methyloxy)phenyl]methyl}oxy)-1,3,11,16-nonadecatetraen-6-ol	C₄₉H₇₄O₉	详情	详情

Extended Information