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【结 构 式】

【分子编号】52372

【品名】2-(hydroxymethyl)-4-(methyloxy)-5-(2-propenyl)tetrahydro-3-furanol

【CA登记号】

【 分 子 式 】C9H16O4

【 分 子 量 】188.22364

【元素组成】C 57.43% H 8.57% O 34%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IX)

Treatment of L-arabinose (I) with tert-butyldiphenylsilyl chloride and imidazole provided the mono-silylated furanose (II). The free hydroxyl groups of (II) were subsequently acylated with Ac2O, yielding the triacetate (III). Introduction of an allyl group in (III) by using the silyl reagent (IV) and boron trifluoride produced the allyl derivative (V) as a diastereomeric mixture. After basic hydrolysis of the acetate esters of (V), the required diastereoisomer (VI) was isolated by means of flash chromatography. Regioselective silylation of diol (VI) with tert-butyldiphenylsilyl chloride furnished (VII). Following methylation of the remaining free hydroxyl, the resultant methyl ether (VIII) was desilylated with methanolic HCl, giving diol (IX). Protection of the primary alcohol of (IX) was accomplished by acylation with pivaloyl chloride in pyridine, yielding (X). The secondary alcohol group of (X) was then converted to the benzyl ether (XI). Subsequent Sharpless asymmetric dihydroxylation of the allyl moiety of (XI) produced glycol (XII).

1 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 52367 4-(acetyloxy)-2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3-furanyl acetate C28H36O6Si 详情 详情
(Vb) 52368 4-(acetyloxy)-2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3-furanyl acetate C28H36O6Si 详情 详情
(I) 52364 2,3,4,5-tetrahydroxypentanal C5H10O5 详情 详情
(II) 52365 5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)tetrahydro-2,3,4-furantriol C21H28O5Si 详情 详情
(III) 52366 2,4-bis(acetyloxy)-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)tetrahydro-3-furanyl acetate C27H34O8Si 详情 详情
(IV) 15775 Allyltrimethylsilane; allyl(trimethyl)silane 762-72-1 C6H14Si 详情 详情
(VI) 52369 2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3,4-furandiol C24H32O4Si 详情 详情
(VII) 52370 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-2-(2-propenyl)tetrahydro-3-furanol C30H46O4Si2 详情 详情
(VIII) 52371 (1,1-dimethylethyl)({[3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-(methyloxy)-5-(2-propenyl)tetrahydro-2-furanyl]methyl}oxy)diphenylsilane; (1,1-dimethylethyl)(dimethyl)silyl 2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-4-(methyloxy)-5-(2-propenyl)tetrahydro-3-furanyl ether C31H48O4Si2 详情 详情
(IX) 52372 2-(hydroxymethyl)-4-(methyloxy)-5-(2-propenyl)tetrahydro-3-furanol C9H16O4 详情 详情
(X) 52373 [3-hydroxy-4-(methyloxy)-5-(2-propenyl)tetrahydro-2-furanyl]methyl 2,2-dimethylpropanoate C14H24O5 详情 详情
(XI) 52374 [4-(methyloxy)-3-[(phenylmethyl)oxy]-5-(2-propenyl)tetrahydro-2-furanyl]methyl 2,2-dimethylpropanoate C21H30O5 详情 详情
(XII) 52375 {5-(2,3-dihydroxypropyl)-4-(methyloxy)-3-[(phenylmethyl)oxy]tetrahydro-2-furanyl}methyl 2,2-dimethylpropanoate C21H32O7 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IX)

Treatment of L-arabinose (I) with tert-butyldiphenylsilyl chloride and imidazole provided the mono-silylated furanose (II). The free hydroxyl groups of (II) were subsequently acylated with Ac2O, yielding the triacetate (III). Introduction of an allyl group in (III) by using the silyl reagent (IV) and boron trifluoride produced the allyl derivative (V) as a diastereomeric mixture. After basic hydrolysis of the acetate esters of (V), the required diastereoisomer (VI) was isolated by means of flash chromatography. Regioselective silylation of diol (VI) with tert-butyldiphenylsilyl chloride furnished (VII). Following methylation of the remaining free hydroxyl group of (VII), the resultant methyl ether (VIII) was desilylated with methanolic HCl, giving diol (IX). Protection of the primary alcohol of (IX) was accomplished by acylation with pivaloyl chloride in pyridine, yielding (X). The secondary alcohol group of (X) was then converted to the benzyl ether (XI). Subsequent Sharpless asymmetric dihydroxylation of the allyl moiety of (XI) produced glycol (XII).

1 Littlefield, B.A.; Zheng, W.; Seletsky, B.M.; Yu, M.J.; Palme, M.H.; Towle, M.J. (Eisai Co., Ltd.); Macrocyclic analogs and methods of their use and preparation. US 6214865; WO 9965894 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 52367 4-(acetyloxy)-2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3-furanyl acetate C28H36O6Si 详情 详情
(Vb) 52368 4-(acetyloxy)-2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3-furanyl acetate C28H36O6Si 详情 详情
(I) 52364 2,3,4,5-tetrahydroxypentanal C5H10O5 详情 详情
(II) 52365 5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)tetrahydro-2,3,4-furantriol C21H28O5Si 详情 详情
(III) 52366 2,4-bis(acetyloxy)-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)tetrahydro-3-furanyl acetate C27H34O8Si 详情 详情
(IV) 15775 Allyltrimethylsilane; allyl(trimethyl)silane 762-72-1 C6H14Si 详情 详情
(VI) 52369 2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-5-(2-propenyl)tetrahydro-3,4-furandiol C24H32O4Si 详情 详情
(VII) 52370 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-2-(2-propenyl)tetrahydro-3-furanol C30H46O4Si2 详情 详情
(VIII) 52371 (1,1-dimethylethyl)({[3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-(methyloxy)-5-(2-propenyl)tetrahydro-2-furanyl]methyl}oxy)diphenylsilane; (1,1-dimethylethyl)(dimethyl)silyl 2-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-4-(methyloxy)-5-(2-propenyl)tetrahydro-3-furanyl ether C31H48O4Si2 详情 详情
(IX) 52372 2-(hydroxymethyl)-4-(methyloxy)-5-(2-propenyl)tetrahydro-3-furanol C9H16O4 详情 详情
(X) 52373 [3-hydroxy-4-(methyloxy)-5-(2-propenyl)tetrahydro-2-furanyl]methyl 2,2-dimethylpropanoate C14H24O5 详情 详情
(XI) 52374 [4-(methyloxy)-3-[(phenylmethyl)oxy]-5-(2-propenyl)tetrahydro-2-furanyl]methyl 2,2-dimethylpropanoate C21H30O5 详情 详情
(XII) 52375 {5-(2,3-dihydroxypropyl)-4-(methyloxy)-3-[(phenylmethyl)oxy]tetrahydro-2-furanyl}methyl 2,2-dimethylpropanoate C21H32O7 详情 详情
Extended Information