SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND THE GLYCOSIDIC COUPLING REACTION OF SUBSTITUTED 2,7-DIOXABICYCLO[4.1.0]HEPTANES - 1,2-ANHYDRO-3,4-DI-O-BENZYL-BETA-L- AND BETA-D-RHAMNOPYRANOSES | |
CHEN, Q; KONG, FZ; CAO, LX | |
刊名 | CARBOHYDRATE RESEARCH |
1993 | |
卷号 | 240期号:1页码:107-117 |
DOI | 10.1016/0008-6215(93)84176-7 |
英文摘要 | 1,2-Anhydro-3,4-di-O-benzyl-alpha-L-rhamnopyranose was synthesized from L-rhamnose, while the D-enantiomer was synthesized from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-mannopyranoside. For both of the syntheses, the key intermediates were 2-O-acetyl-3,4-di-O-benzyl-alpha-D- and -alpha-L-rhamnopyranosyl chlorides that were quantitatively prepared from the corresponding diacetates by chlorination. Ring closure of the chlorides was carried out readily with potassium tert-butoxide in oxolane, and crystalline 1,2-anhydro-3,4-di-O-benzyl-beta-D- and beta-L-rhamnopyranose were obtained in high yields. Conformational calculations, which were carried out using vicinal proton-proton coupling constants by the modified Karplus equation, suggested that the conformations of the pyranose rings of the title compounds were basically a half chair (H4(5)) with some flattening at C-4. Force-field calculations (MMP2) confirmed the experimental conformation with good agreement. The coupling reaction of the 1,2-anhydro-L-rhamnose ether with 1,2;3,4-di-O-isopropylidene-a-D-galactopyranose was effected in oxolane by catalysis by a Lewis acid, and only the alpha-linked disaccharide was obtained. |
WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
WOS记录号 | WOS:A1993KP61500010 |
内容类型 | 期刊论文 |
源URL | [http://ir.rcees.ac.cn/handle/311016/24488] |
专题 | 生态环境研究中心_中国科学院环境生物技术重点实验室 |
推荐引用方式 GB/T 7714 | CHEN, Q,KONG, FZ,CAO, LX. SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND THE GLYCOSIDIC COUPLING REACTION OF SUBSTITUTED 2,7-DIOXABICYCLO[4.1.0]HEPTANES - 1,2-ANHYDRO-3,4-DI-O-BENZYL-BETA-L- AND BETA-D-RHAMNOPYRANOSES[J]. CARBOHYDRATE RESEARCH,1993,240(1):107-117. |
APA | CHEN, Q,KONG, FZ,&CAO, LX.(1993).SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND THE GLYCOSIDIC COUPLING REACTION OF SUBSTITUTED 2,7-DIOXABICYCLO[4.1.0]HEPTANES - 1,2-ANHYDRO-3,4-DI-O-BENZYL-BETA-L- AND BETA-D-RHAMNOPYRANOSES.CARBOHYDRATE RESEARCH,240(1),107-117. |
MLA | CHEN, Q,et al."SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND THE GLYCOSIDIC COUPLING REACTION OF SUBSTITUTED 2,7-DIOXABICYCLO[4.1.0]HEPTANES - 1,2-ANHYDRO-3,4-DI-O-BENZYL-BETA-L- AND BETA-D-RHAMNOPYRANOSES".CARBOHYDRATE RESEARCH 240.1(1993):107-117. |
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