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【结 构 式】

【分子编号】57366

【品名】(2S)-1-{2-[(4-methoxybenzyl)oxy]acetyl}-2-piperidinecarboxylic acid

【CA登记号】

【 分 子 式 】C16H21NO5

【 分 子 量 】307.34648

【元素组成】C 62.53% H 6.89% N 4.56% O 26.03%

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:(XLVIII)

The silylation of the remaining OH group of (XLV) with Tes-OTf and lutidine in dichloromethane gives the fully silylated intermediate (XLVI), which is treated with a mild acid in order to cleave the 1,3-dithiane ring and yield the carbaldehyde (XLVII). The condensation of (XLVII) with the chiral piperidine carboxylic acid (XLVIII) by means of LDA in THF affords the adduct (XLIX). The oxidation of the OH group of (XLIX) provides the beta dioxo compound (L), which is treated with Ac-OH in THF/water to selectively cleave the triethylsilyl protecting group and yield the secondary alcohol (LI).

1 Chen, K.; Formal total synthesis of (-)-FK506. Diss Abstr Int B - Sci Eng 1993, 53, 9, 4663.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XLV) 57363 (1E,3S,4S,5S,7R,8R,9E,12S,14S,15R,16S,18R)-8-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-14,16,19,19-tetramethoxy-1-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-2,4,10,12,18-pentamethyl-5-[(triisopropylsilyl)oxy]-1,9-nonadecadien-3-ol C68H138O10Si4 详情 详情
(XLVI) 57364 (1S,2R,3S,5S,7E,9R,10R,12S,13S,14S,15E)-9-allyl-2,10-bis{[tert-butyl(dimethyl)silyl]oxy}-1-[(2R)-3,3-dimethoxy-2-methylpropyl]-3-methoxy-16-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-5,7,13,15-tetramethyl-14-[(triethylsilyl)oxy]-12-[(triisopropylsilyl)oxy]-7,15-hexadecadienyl methyl ether C74H152O10Si5 详情 详情
(XLVII) 57365 (2R,4S,5R,6S,8S,10E,12R,13R,15S,16S,17S,18E)-12-allyl-5,13-bis{[tert-butyl(dimethyl)silyl]oxy}-4,6-dimethoxy-19-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-2,8,10,16,18-pentamethyl-17-[(triethylsilyl)oxy]-15-[(triisopropylsilyl)oxy]-10,18-nonadecadienal C72H146O9Si5 详情 详情
(XLVIII) 57366 (2S)-1-{2-[(4-methoxybenzyl)oxy]acetyl}-2-piperidinecarboxylic acid C16H21NO5 详情 详情
(XLIX) 57367 (2S)-1-{(4R,6S,7R,8S,10S,12E,14R,15R,17S,18S,19S,20E)-14-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-6,8-dimethoxy-2-[(4-methoxybenzyl)oxy]-21-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-4,10,12,18,20-pentamethyl-19-[(triethylsilyl)oxy]-17-[(triisopropylsilyl)oxy]-12,20-henicosadienoyl}-2-piperidinecarboxylic acid C88H167NO14Si5 详情 详情
(L) 57368 (2S)-1-{(4R,6S,7R,8S,10S,12E,14R,15R,17S,18S,19S,20E)-14-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-6,8-dimethoxy-2-[(4-methoxybenzyl)oxy]-21-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-4,10,12,18,20-pentamethyl-3-oxo-19-[(triethylsilyl)oxy]-17-[(triisopropylsilyl)oxy]-12,20-henicosadienoyl}-2-piperidinecarboxylic acid C88H165NO14Si5 详情 详情
(LI) 57369 (2S)-1-{(4R,6S,7R,8S,10S,12E,14R,15R,17S,18S,19S,20E)-14-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-19-hydroxy-6,8-dimethoxy-2-[(4-methoxybenzyl)oxy]-21-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-4,10,12,18,20-pentamethyl-3-oxo-17-[(triisopropylsilyl)oxy]-12,20-henicosadienoyl}-2-piperidinecarboxylic acid C82H151NO14Si4 详情 详情
Extended Information