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【结 构 式】

【分子编号】42479

【品名】(2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-4-[(triethylsilyl)oxy]butanal

【CA登记号】

【 分 子 式 】C17H38O3Si2

【 分 子 量 】346.65792

【元素组成】C 58.9% H 11.05% O 13.85% Si 16.2%

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:(XXXIV)

The oxidation of (XXV) with DMP in dichloromethane gives the aldehyde (XXVII), which is condensed with phosphorane (XXVIII) in refluxing toluene to yield aldehyde (XXIX). The reduction of (XXIX) with Zn(BH4)2 in ethyl ether affords alcohol (XXX), which is condensed with 2-sulfanylbenzothiazole (XXXI) by means of Bu3P and TMAD in benzene providing the thioether (XXXII). The oxidation of (XXXII) with Mo7O24(NH4)6 and H2O2 in ethanol gives the sulfone (XXXIII), which is condensed with the aldehyde (XXXIV) by means of LHMDS in THF to yield intermediate (XXXV). The selective monodesilylation of (XXXV) with PPTS in chloroform/methanol, followed by oxidation with DMP, affords the aldehyde (XXXVI).

1 Shimizu, T.; et al.; Total synthesis of reveromycin A. Org Lett 2000, 2, 14, 2153.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXV) 42472 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-8-(2-hydroxyethyl)-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl] succinate C32H48O9 详情 详情
(XXVII) 42474 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-9-methyl-8-(2-oxoethyl)-1,7-dioxaspiro[5.5]undec-3-yl] succinate C32H46O9 详情 详情
(XXVIII) 39940 2-(triphenylphosphoranylidene)propanal C21H19OP 详情 详情
(XXIX) 42475 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-9-methyl-8-[(E)-3-methyl-4-oxo-2-butenyl]-1,7-dioxaspiro[5.5]undec-3-yl] succinate C35H50O9 详情 详情
(XXX) 42476 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-8-[(E)-4-hydroxy-3-methyl-2-butenyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl] succinate C35H52O9 详情 详情
(XXXI) 24677 1,3-benzothiazol-2-ylhydrosulfide 149-30-4 C7H5NS2 详情 详情
(XXXII) 42477 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-8-[(E)-4-(1,3-benzothiazol-2-ylsulfanyl)-3-methyl-2-butenyl]-3-butyl-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl] succinate C42H55NO8S2 详情 详情
(XXXIII) 42478 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-8-[(E)-4-(1,3-benzothiazol-2-ylsulfonyl)-3-methyl-2-butenyl]-3-butyl-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl] succinate C42H55NO10S2 详情 详情
(XXXIV) 42479 (2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-methyl-4-[(triethylsilyl)oxy]butanal C17H38O3Si2 详情 详情
(XXXV) 42480 1-allyl 4-((2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-8-[(2E,4E,6S,7S)-6-[[tert-butyl(dimethyl)silyl]oxy]-3,7-dimethyl-8-[(triethylsilyl)oxy]-2,4-octadienyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl) succinate C52H88O10Si2 详情 详情
(XXXVI) 42481 1-allyl 4-[(2S,3R,6S,8R,9S)-2-[(1E,3E)-5-(allyloxy)-3-methyl-5-oxo-1,3-pentadienyl]-3-butyl-8-((2E,4E,6S,7R)-6-[[tert-butyl(dimethyl)silyl]oxy]-3,7-dimethyl-8-oxo-2,4-octadienyl)-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl] succinate C46H72O10Si 详情 详情
Extended Information