Ethyl 6-hydroxyhexanoate → 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside
반응식
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Cl)(=[O:3])[CH3:2].[CH2:25]([O:27][C:28]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])=[O:29])[CH3:26]>C(Cl)(Cl)Cl>[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C:28]([O:27][CH2:25][CH3:26])=[O:29])(=[O:3])[CH3:2]참가 물질
4
실험 절차
Condensation of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride with 5-ethoxycarbonyl-1-pentanol under the same conditions as reported in example II gave a 74% yield of 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside, mp 101°-102°, [α]D25 - 16.8° (c 1.06, chloroform). De-O-acetylation of this compound using sodium methoxide gave after crystallization a 92% yield of 4 mp 154°-155° (melts and resolidifies) remelts 167°, [α]D18 - 25.5° (c 1.1, water).