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【结 构 式】

【分子编号】42678

【品名】(5R,6S,7Z,10S,11R)-11-[(1R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]ethyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-5-[(1S)-1-methyl-2-(trityloxy)ethyl]-4,12-dioxa-3,13-disila-7-pentadecene; (2S,3R,4S,5Z,8S,9R,10R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-10-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-2,4,6,8-tetramethyl-5-undecenyl trityl ether

【CA登记号】

【 分 子 式 】C58H86O6Si2

【 分 子 量 】935.48824

【元素组成】C 74.47% H 9.27% O 10.26% Si 6%

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:(XXVIII)

The target compound has been obtained as follows: The reaction of intermediate iodo derivative (XV) with ZnCl2 and BuLi gives the organozinc compound (XXVI), which is condensed with intermediate iodo derivative (XVIII) by means of Pd(PPh3)4, yielding the adduct (XXVII). The selective deprotection of the Pmb group of (XXVII) with DDQ, followed by reprotection with Tr-Cl, affords the suitably protected adduct (XXVIII). Cleaving of the cyclic ketal group of (XXVIII) with DIBAL provides the primary alcohol (XXIX), which is oxidized with DMP, giving the aldehyde (XXX). The condensation of (XXX) with the titanium derivative (XXXI) yields the adduct (XXXII), which is selectively deprotected at the trityl group with chloro-catecholborane to afford the primary alcohol (XXXIII). The reaction of (XXXIII) with PPh3 , I2 and DIEA furnishes the phosphonium iodide (XXXIV).

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 CAS号 分子式 供应商 用于合成
(XV) 42665 tert-butyl(dimethyl)silyl (1S,2R)-3-iodo-1-[(1R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]ethyl]-2-methylpropyl ether; tert-butyl[((1S,2R)-3-iodo-1-[(1R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]ethyl]-2-methylpropyl)oxy]dimethylsilane C24H41IO4Si 详情 详情
(XVIII) 42668 tert-butyl(dimethyl)silyl (1R,2S,3Z)-4-iodo-1-[(1S)-2-[(4-methoxybenzyl)oxy]-1-methylethyl]-2-methyl-3-pentenyl ether; tert-butyl[((1R,2S,3Z)-4-iodo-1-[(1S)-2-[(4-methoxybenzyl)oxy]-1-methylethyl]-2-methyl-3-pentenyl)oxy]dimethylsilane C23H39IO3Si 详情 详情
(XXVI) 42676 tert-butyl[(2R,3S,4R)-3-[[tert-butyl(dimethyl)silyl]oxy]-4-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-2-methylpentyl]zinc C28H50O4SiZn 详情 详情
(XXVII) 42677 (5R,6S,7Z,10S,11R)-5-[(1S)-2-[(4-methoxybenzyl)oxy]-1-methylethyl]-11-[(1R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]ethyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disila-7-pentadecene; 4-((4S,5S)-4-[(1R,2R,3S,5Z,7S,8R,9S)-2,8-bis[[tert-butyl(dimethyl)silyl]oxy]-10-[(4-methoxybenzyl)oxy]-1,3,5,7,9-pentamethyl-5-decenyl]-5-methyl-1,3-dioxan-2-yl)phenyl methyl ether C47H80O7Si2 详情 详情
(XXVIII) 42678 (5R,6S,7Z,10S,11R)-11-[(1R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]ethyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-5-[(1S)-1-methyl-2-(trityloxy)ethyl]-4,12-dioxa-3,13-disila-7-pentadecene; (2S,3R,4S,5Z,8S,9R,10R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-10-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-2,4,6,8-tetramethyl-5-undecenyl trityl ether C58H86O6Si2 详情 详情
(XXIX) 42679 (2S,3S,4R,5R,6S,8Z,10S,11R,12S)-5,11-bis[[tert-butyl(dimethyl)silyl]oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10,12-hexamethyl-13-(trityloxy)-8-tridecen-1-ol C58H88O6Si2 详情 详情
(XXX) 42680 (2R,3R,4R,5R,6S,8Z,10S,11R,12S)-5,11-bis[[tert-butyl(dimethyl)silyl]oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10,12-hexamethyl-13-(trityloxy)-8-tridecenal C58H86O6Si2 详情 详情
(XXXI) 42681   C39H34LiO4PTi 详情 详情
(XXXII) 42682 (2S,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 trityl ether; (5R,6S,7Z,10S,11R)-11-[(1R,2S,3S,4Z)-2-[(4-methoxybenzyl)oxy]-1,3-dimethyl-4,6-heptadienyl]-2,2,3,3,6,8,10,13,13,14,14-undecamethyl-5-[(1S)-1-methyl-2-(trityloxy)ethyl]-4,12-dioxa-3,13-disila-7-pentadecene C61H90O5Si2 详情 详情
(XXXIII) 42683 (2S,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-hexadecatrien-1-ol C42H76O5Si2 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
Extended Information