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【结 构 式】

【分子编号】42432

【品名】triisopropyl([(1S,3R,4S,5R,6S)-4-methyl-5-[(triisopropylsilyl)oxy]-2,7-dioxabicyclo[4.1.0]hept-3-yl]methoxy)silane; [(1S,3R,4S,5R,6S)-4-methyl-5-[(triisopropylsilyl)oxy]-2,7-dioxabicyclo[4.1.0]hept-3-yl]methyl triisopropylsilyl ether

【CA登记号】

【 分 子 式 】C25H52O4Si2

【 分 子 量 】472.85648

【元素组成】C 63.5% H 11.08% O 13.53% Si 11.88%

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:(LXXI)

Synthesis of intermediate (LXXI): The reaction of aldehyde (LXIV) with (S,S)-diisopropyl-(E)-crotyl boronate (DISCB) in toluene gives the alcohol (LXV), which is protected with Bn-Br and NaH yielding the benzyl ether (LXVI). The oxidation of the terminal double bond of (LXVI) with OsO4 and NaIO4 affords the aldehyde (LXVII), which is treated with (DISAB) to provide the allyl alcohol (LVIII). The silylation of (LXVIII) with Tips-OTf, followed by debenzylation with Li/NH3, gives the expected disilylated triol (LXIX). The oxidation of the terminal double bond of (LXIX) with OsO4 and NaIO4, with simultaneous cyclization yields the dihydropyran derivative (LXX), which is epoxidated with dimethyldioxirane (DMDO) in dichloromethane/acetone to afford the desired epoxide intermediate (LXXI).

1 Hayward, M.M.; et al.; Total synthesis of altohyrtin A (spongistatin 1): Part 2. Angew Chem. Int Ed Engl 1998, 37, 1-2, 192.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(LV) 42415 tributyl(2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-propenyl)stannane C21H42O2Sn 详情 详情
(LXIV) 42425 2-[(triisopropylsilyl)oxy]acetaldehyde C11H24O2Si 详情 详情
(LXV) 42426 (2R,3R)-3-methyl-1-[(triisopropylsilyl)oxy]-4-penten-2-ol C15H32O2Si 详情 详情
(LXVI) 42427 benzyl (1R,2R)-2-methyl-1-[[(triisopropylsilyl)oxy]methyl]-3-butenyl ether; [[(2R,3R)-2-(benzyloxy)-3-methyl-4-pentenyl]oxy](triisopropyl)silane C22H38O2Si 详情 详情
(LXVII) 42428 (2S,3R)-3-(benzyloxy)-2-methyl-4-[(triisopropylsilyl)oxy]butanal C21H36O3Si 详情 详情
(LXVIII) 42429 (4S,5R,6R)-6-(benzyloxy)-5-methyl-7-[(triisopropylsilyl)oxy]-1-hepten-4-ol C24H42O3Si 详情 详情
(LXIX) 42430 (5S,6S,7R)-5-allyl-7-(benzyloxy)-3,3,10,10-tetraisopropyl-2,6,11-trimethyl-4,9-dioxa-3,10-disiladodecane; benzyl (1R,2S,3S)-2-methyl-3-[(triisopropylsilyl)oxy]-1-[[(triisopropylsilyl)oxy]methyl]-5-hexenyl ether C33H62O3Si2 详情 详情
(LXX) 42431 triisopropyl([(2R,3S,4R)-3-methyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-pyran-2-yl]methoxy)silane; [(2R,3S,4R)-3-methyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-pyran-2-yl]methyl triisopropylsilyl ether C25H52O3Si2 详情 详情
(LXXI) 42432 triisopropyl([(1S,3R,4S,5R,6S)-4-methyl-5-[(triisopropylsilyl)oxy]-2,7-dioxabicyclo[4.1.0]hept-3-yl]methoxy)silane; [(1S,3R,4S,5R,6S)-4-methyl-5-[(triisopropylsilyl)oxy]-2,7-dioxabicyclo[4.1.0]hept-3-yl]methyl triisopropylsilyl ether C25H52O4Si2 详情 详情
(LXXII) 42433 (2R,3R,4R,5S,6R)-2-(2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-propenyl)-5-methyl-4-[(triisopropylsilyl)oxy]-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-3-ol C34H68O6Si2 详情 详情
(LXXIII) 42434 (2R,3S,4R,5R,6R)-2-(2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-propenyl)-6-(hydroxymethyl)-5-methyltetrahydro-2H-pyran-3,4-diol C16H28O6 详情 详情
(LXXIV) 42435 tert-butyl(dimethyl)silyl [(2R,3R,4R,5S,6R)-6-(2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-propenyl)-4,5-bis[(4-methoxybenzyl)oxy]-3-methyltetrahydro-2H-pyran-2-yl]methyl ether; tert-butyl([(2R,3R,4R,5S,6R)-6-(2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-propenyl)-4,5-bis[(4-methoxybenzyl)oxy]-3-methyltetrahydro-2H-pyran-2-yl]methoxy)dimethylsilane C38H58O8Si 详情 详情
(LXXV) 42436 (2S)-4-([(2R,3S,4R,5R,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,4-bis[(4-methoxybenzyl)oxy]-5-methyltetrahydro-2H-pyran-2-yl]methyl)-2-hydroxy-4-pentenyl pivalate C40H62O9Si 详情 详情
(LXXVI) 42437 (2S)-4-([(2R,3S,4R,5R,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,4-bis[(4-methoxybenzyl)oxy]-5-methyltetrahydro-2H-pyran-2-yl]methyl)-2-[(triisopropylsilyl)oxy]-4-penten-1-ol C44H74O8Si2 详情 详情
(LXXVII) 42438 (2S)-4-([(2R,3S,4R,5R,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,4-bis[(4-methoxybenzyl)oxy]-5-methyltetrahydro-2H-pyran-2-yl]methyl)-2-[(triisopropylsilyl)oxy]-4-pentenal C44H72O8Si2 详情 详情
(LXXVIII) 31608 2,3-dichloro-1-propene 78-88-6 C3H4Cl2 详情 详情
(LXXIX) 42439 ([(1S,2E)-1-[2-([(2R,3S,4R,5R,6R)-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-3,4-bis[(4-methoxybenzyl)oxy]-5-methyltetrahydro-2H-pyran-2-yl]methyl)-2-propenyl]-4-chloro-2,4-pentadienyl]oxy)(triisopropyl)silane; tert-butyl(dimethyl)silyl [(2R,3R,4R,5S,6R)-6-[(4S,5E)-7-chloro-2-methylene-4-[(triisopropylsilyl)oxy]-5,7-octadienyl]-4,5-bis[(4-methoxybenzyl)oxy]-3-methyltetrahydro-2H-pyran-2-yl]methyl ether C47H75ClO7Si2 详情 详情
(LXXX) 42440 (2R,3R,4R,5S,6R)-6-[(4S,5E)-7-chloro-2-methylene-4-[(triisopropylsilyl)oxy]-5,7-octadienyl]-4,5-bis[(4-methoxybenzyl)oxy]-3-methyltetrahydro-2H-pyran-2-carbaldehyde C41H59ClO7Si 详情 详情
Extended Information