(3S,4S,5S,6E)-7-[(1R,3R,4R)-3-Methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-3-[(triisopropylsilyl)oxy]-6-heptenal -Drug Synthesis Database

【结构式】

【分子编号】11545

【品名】(3S,4S,5S,6E)-7-[(1R,3R,4R)-3-Methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-3-[(triisopropylsilyl)oxy]-6-heptenal

【CA登记号】

【分子式】C₄₀H₈₂O₅Si₃

【分子量】727.34458

【元素组成】C 66.05% H 11.36% O 11% Si 11.58%

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：(XLVI)

(XLIII) is silylated with TIPS-SO3CF3 to the protected ester (XLIV). The reduction of (XLIV) with diisobutylaluminum hydride yields the primary alcohol (XLV), which is oxidized with the complex pyridine - SO3 to the aldehyde (XLVI). The condensation of (XLVI) with the boron enolate of the oxazolidone (XLVII) affords the oxazolidone derivative (XLVIII), which is treated with methylchloroaluminum N-methoxy-N-methylamide as before to give the methoxyamide (XLIX). Silylation of (XLIX) with TBS-SO3CF3 as usual yields the protected amide (L), which is finally reduced with diisobutylaluminum hydride to the second building group, the aldehyde (LI).

参考文献中间体

合成目标

【1】 Jones, T.K.; Askin, D.; Mills, S.G.; Reamer, R.A.; Desmond, R.; Volante, R.P.; Tschaen, D.M.; Shinkai, I. (Merck & Co., Inc.); Process for synthesis of FK-506 and tricarbonyl intermediates. EP 0378318; JP 1990233643 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
	63306		C₃H₉AlClNO	详情	详情
(IL)	11548	(2S,3S,5S,6S,7S,8E)-2-Allyl-3-hydroxy-N-methoxy-9-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-N,6,8-trimethyl-7-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-8-nonenamide	C₄₇H₉₅NO₇Si₃	详情	详情
(XLIII)	11542	methyl (3S,4R,5S,6E)-3-hydroxy-7-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-6-heptenoate	C₃₂H₆₄O₆Si₂	详情	详情
(XLIV)	11543	methyl (3S,4S,5S,6E)-7-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-3-[(triisopropylsilyl)oxy]-6-heptenoate	C₄₁H₈₄O₆Si₃	详情	详情
(XLV)	11544	(3S,4S,5S,6E)-7-[(1R,3R,4R)-3-Methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-3-[(triisopropylsilyl)oxy]-6-hepten-1-ol	C₄₀H₈₄O₅Si₃	详情	详情
(XLVI)	11545	(3S,4S,5S,6E)-7-[(1R,3R,4R)-3-Methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-4,6-dimethyl-5-[(triethylsilyl)oxy]-3-[(triisopropylsilyl)oxy]-6-heptenal	C₄₀H₈₂O₅Si₃	详情	详情
(XLVII)	11546	(4S)-4-Isopropyl-3-(4-pentenoyl)-1,3-oxazolidin-2-one	C₁₁H₁₇NO₃	详情	详情
(XLVIII)	11547	(4S)-3-[(2S,3S,5S,6S,7S,8E)-2-Allyl-3-hydroxy-9-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-6,8-dimethyl-7-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-8-nonenoyl]-4-isopropyl-1,3-oxazolidin-2-one	C₅₁H₉₉NO₈Si₃	详情	详情
(L)	11549	(2S,3S,5S,6S,7S,8E)-2-Allyl-3-[[tert-butyl(dimethyl)silyl]oxy]-N-methoxy-9-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-N,6,8-trimethyl-7-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-8-nonenamide	C₅₃H₁₀₉NO₇Si₄	详情	详情
(LI)	11550	(2S,3S,5S,6S,7S,8E)-2-Allyl-3-[[tert-butyl(dimethyl)silyl]oxy]-9-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-6,8-dimethyl-7-[(triethylsilyl)oxy]-5-[(triisopropylsilyl)oxy]-8-nonenal	C₅₁H₁₀₄O₆Si₄	详情	详情

Extended Information