• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】63888

【品名】(E)-3-(tributylstannyl)-2-propenal

【CA登记号】

【 分 子 式 】C15H30OSn

【 分 子 量 】345.1126

【元素组成】C 52.2% H 8.76% O 4.64% Sn 34.4%

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:(XXVI)

Synthesis of the target Laulimalide. The condensation of the tin derivative (XXVI) with the chiral isopropenyl boron derivative (XXVII) gives the secondary alcohol (XXVIII), which is alkylated with allyl bromide (XXIX) and KHMDS to yield the allyl ether (XXX). The ring closing metathesis reaction in (XXX) by means of Schrock catalyst affords the dihydropyranyl stannane (XXXI), which is treated with N-iodosuccinimide to provide the iodovinyl compound (XXXII). The reaction of (XXXII) with BuLi and MgBr2 gives the vinylmagnesium derivative (XXXIII), which is condensed with the unsaturated aldehyde intermediate (XXV) to yield the olefinic alcohol (XXXIV). The reaction of (XXXIV) with Tbdms-Cl and imidazole affords the silyl ether (XXXV), which is selectively deprotected with formic acid, and oxidated with DMP to provide the chiral unsaturated aldehyde (XXXVI).

1 Nelson, S.G.; Cheung, W.S.; Kassick, A.J.; Hilfiker, M.A.; A de novo enantioselective total synthesis of (-)-laulimalide. J Am Chem Soc 2002, 124, 46, 13654.
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) 63887 (2S,4E)-2-[(4-methoxybenzyl)oxy]-6-(trityloxy)-4-hexenal C33H32O4 详情 详情
(XXVI) 63888 (E)-3-(tributylstannyl)-2-propenal C15H30OSn 详情 详情
(XXVII) 63889   C5H11B 详情 详情
(XXVIII) 63890 (1E)-5-methyl-1-(tributylstannyl)-1,5-hexadien-3-ol C19H38OSn 详情 详情
(XXIX) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(XXX) 63891 [(1E)-3-(allyloxy)-5-methyl-1,5-hexadienyl](tributyl)stannane; allyl 3-methyl-1-[(E)-2-(tributylstannyl)ethenyl]-3-butenyl ether C22H42OSn 详情 详情
(XXXI) 63894 tributyl{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}stannane C20H38OSn 详情 详情
(XXXII) 63893 (2S)-2-[(E)-2-iodoethenyl]-4-methyl-3,6-dihydro-2H-pyran C8H11IO 详情 详情
(XXXIII) 63892 bromo{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}magnesium C8H11BrMgO 详情 详情
(XXXIV) 63895 (1E,3S,4S,6E)-4-[(4-methoxybenzyl)oxy]-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-8-(trityloxy)-1,6-octadien-3-ol C41H44O5 详情 详情
(XXXV) 63896 tert-butyl(dimethyl)silyl (1S,2S,4E)-2-[(4-methoxybenzyl)oxy]-1-{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}-6-(trityloxy)-4-hexenyl ether; tert-butyl{[(1S,2S,4E)-2-[(4-methoxybenzyl)oxy]-1-{(E)-2-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]ethenyl}-6-(trityloxy)-4-hexenyl]oxy}dimethylsilane C47H58O5Si 详情 详情
(XXXVI) 63897 (2E,5S,6S,7E)-6-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-2,7-octadienal C28H42O5Si 详情 详情
Extended Information