tert-butyl(dimethyl)silyl (2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl ether; tert-butyl([(2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl]oxy)dimethylsilane -Drug Synthesis Database

【结构式】

【分子编号】42723

【品名】tert-butyl(dimethyl)silyl (2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl ether; tert-butyl([(2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl]oxy)dimethylsilane

【CA登记号】

【分子式】C₂₂H₃₈O₃Si

【分子量】378.62742

【元素组成】C 69.79% H 10.12% O 12.68% Si 7.42%

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：(XLIV)

The diol (XLVII) has been obtained as follows: The Swern oxidation of the OH groups of (XLVII) gives the 5-oxohexanal derivative (XLVIII), which is condensed with the phosphonium salt (XXXVI) to yield the iodovinyl derivative (XLIX). Finally, this compound is homologated with vinylzinc bromide (XXXVIII) to afford the target intermediate ketone (XLIII).

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
(XVII)	42701	(2S,3R,4S)-1-[[tert-butyl(dimethyl)silyl]oxy]-2,4-dimethyl-5-hexen-3-ol		C₁₄H₃₀O₂Si	详情	详情
(XXXVI)	42718	(iodomethyl)(triphenyl)phosphonium iodide	n/a	C₁₉H₁₇I₂P	详情	详情
(XXXVIII)	42720	bromo(vinyl)zinc	n/a	C₂H₃BrZn	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
(XLIV)	42723	tert-butyl(dimethyl)silyl (2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl ether; tert-butyl([(2S,3R,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-hexenyl]oxy)dimethylsilane		C₂₂H₃₈O₃Si	详情	详情
(XLV)	42724	(2R,3S,4S)-5-[[tert-butyl(dimethyl)silyl]oxy]-3-[(4-methoxybenzyl)oxy]-2,4-dimethylpentanal		C₂₁H₃₆O₄Si	详情	详情
(XLVI)	42725	(3S,4S,5S)-6-[[tert-butyl(dimethyl)silyl]oxy]-4-[(4-methoxybenzyl)oxy]-3,5-dimethyl-2-hexanol	n/a	C₂₂H₄₀O₄Si	详情	详情
(XLVII)	42726	(2S,3S,4S)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-1,5-hexanediol	n/a	C₁₆H₂₆O₄	详情	详情
(XLVIII)	42727	(2R,3S,4R)-3-[(4-methoxybenzyl)oxy]-2,4-dimethyl-5-oxohexanal		C₁₆H₂₂O₄	详情	详情
(XLIX)	42728	(3R,4S,5S,6Z)-7-iodo-4-[(4-methoxybenzyl)oxy]-3,5-dimethyl-6-hepten-2-one		C₁₇H₂₃IO₃	详情	详情

Extended Information