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【结 构 式】

【分子编号】40916

【品名】(2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde

【CA登记号】

【 分 子 式 】C21H24O3

【 分 子 量 】324.41976

【元素组成】C 77.75% H 7.46% O 14.8%

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:(XXX)

The esterification of (rac)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (XXII) with diazomethane gives the methyl ester (XXIII), which is treated with Bn-Br and K2CO3 yielding the benzyl ether (XXIV). The reduction of the ester group of (XXIV) with LiAlH4 provides the carbinol (XXV), which is debenzylated with H2 over Pd/C to afford the racemic phenol (rac)-(XXVI). Optical resolution of (XXVI) by means of lipase PL-266 and vinyl acetate gives the chiral acetate (S)-(XXVII), which is rebenzylated with BnBr yielding the benzyl ether (XXVIII). The deacetylation of (XXVIII) with LiAlH4 in ethyl ether affords the carbinol (XXIX), which is oxidized with oxalyl chloride to the aldehyde (XXX). The condensation of (XXX) with the intermediate phosphonium salt (XXI) by means of n-BuLi in THF gives the olefin (XXXI), which is finally hydrogenated and debenzylated with H2 over Pd/C in ethyl acetate.

1 Nozawa, M.; et al.; Enantioselective synthesis of (2R,4'R,8'R)-alpha-tocopherol (vitamin E) based on enzymatic function. Chem Pharm Bull 2000, 48, 2, 272.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXI) 40910 triphenyl[(3R,7R)-3,7,11-trimethyldodecyl]phosphonium bromide C33H46BrP 详情 详情
(XXII) 21255 Trolox; Trolox C; 6-hydroxy-2,5,7,8-tetramethyl-2-chromanecarboxylic acid 53188-07-1 C14H18O4 详情 详情
(XXIII) 40911 methyl 6-hydroxy-2,5,7,8-tetramethyl-2-chromanecarboxylate C15H20O4 详情 详情
(XXIV) 40912 methyl 6-(benzyloxy)-2,5,7,8-tetramethyl-2-chromanecarboxylate C22H26O4 详情 详情
(XXV) 18084 [6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanol C21H26O3 详情 详情
(XXVI) 21256 2-(hydroxymethyl)-2,5,7,8-tetramethyl-6-chromanol C14H20O3 详情 详情
(XXVII) 40913 [(2S)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl acetate C16H22O4 详情 详情
(XXVIII) 40914 [(2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl acetate C23H28O4 详情 详情
(XXIX) 40915 [(2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanol C21H26O3 详情 详情
(XXX) 40916 (2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carbaldehyde C21H24O3 详情 详情
(XXXI) 40917 (2S)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-[(E,4R,8R)-4,8,12-trimethyl-1-tridecenyl]-3,4-dihydro-2H-chromene; benzyl (2S)-2,5,7,8-tetramethyl-2-[(E,4R,8R)-4,8,12-trimethyl-1-tridecenyl]-3,4-dihydro-2H-chromen-6-yl ether C36H54O2 详情 详情
Extended Information