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【结 构 式】

【分子编号】59013

【品名】(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate

【CA登记号】

【 分 子 式 】C10H19NO7

【 分 子 量 】265.2634

【元素组成】C 45.28% H 7.22% N 5.28% O 42.22%

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:(IV)

Esterification of glucose diacetonide (I) with N-Boc-gamma-aminobutyric acid (II) in the presence of DCC and DMAP provides the protected glucose-3-ester (III). Hydrolysis of (III) with trifluoroacetic acid in CH2Cl2 leads to the 3-GABA-glucose (IV).

1 Jacob, J.N. (Organomed Corporation); Paclitaxel-carbohydrate conjugates: Design, synthesis and biological evaluations. US 6218367 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 59011 (5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol C12H20O6 详情 详情
(II) 39226 4-[(tert-butoxycarbonyl)amino]butyric acid;4-((tert-butoxycarbonyl)amino)butanoic acid 57294-38-9 C9H17NO4 详情 详情
(III) 59012 (5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-[(tert-butoxycarbonyl)amino]butanoate C21H35NO9 详情 详情
(IV) 59013 (3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate C10H19NO7 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Condensation of paclitaxel (V) with succinic anhydride (VI) affords the hemisuccinate ester (VII). This is subsequently coupled with amino ester (IV) in the presence of DCC to furnish the title compound.

1 Jacob, J.N. (Organomed Corporation); Paclitaxel-carbohydrate conjugates: Design, synthesis and biological evaluations. US 6218367 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 59013 (3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate C10H19NO7 详情 详情
(V) 10595 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 33069-62-4 C47H51NO14 详情 详情
(VI) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(VII) 59014 4-{[(1R,2S)-2-(benzoylamino)-1-({[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl]oxy}carbonyl)-2-phenylethyl]oxy}-4-oxobutano C51H55NO17 详情 详情
Extended Information