ethyl 4-O-methyl-β-D-gluco-pyranoside | 38953-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-methyl-β-D-gluco-pyranoside
• 英文别名: Aethyl 4-O-methyl-β-D-glucopyranosid；Ethyl-4-O-methyl-β-D-glucopyranosid；(2R,3R,4R,5S,6R)-2-ethoxy-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol
• CAS: 38953-93-4
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: YTNQDNTUAJSVQW-JGKVKWKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 ethyl 4-O-methyl-β-D-gluco-pyranoside 在 camphor-10-sulfonic acid 作用下， 生成 methyl 4-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Transglucosidation of methyl and ethyl d-glucopyranosides by alcoholysis

  摘要：

  The transglucosidations of methyl 4-0-methyl-alpha- and -beta-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-0-methyl-alpha- and -beta-D-glueopyranoside in methanolic camphor-10-sutfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product ( approximate to 59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00005-8
• 作为产物：
  描述：

  乙醇 、 methyl 4-O-methyl-β-D-glucopyranoside 在 camphor-10-sulfonic acid 作用下， 生成 ethyl 4-O-methyl-β-D-gluco-pyranoside
  参考文献：
  名称：

  Transglucosidation of methyl and ethyl d-glucopyranosides by alcoholysis

  摘要：

  The transglucosidations of methyl 4-0-methyl-alpha- and -beta-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-0-methyl-alpha- and -beta-D-glueopyranoside in methanolic camphor-10-sutfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product ( approximate to 59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00005-8

文献信息

• Transglucosidation of methyl and ethyl d-glucopyranosides by alcoholysis
  作者：Per J Garegg、Karl-Jonas Johansson、Peter Konradsson、Bengt Lindberg、Zygmunt Trumpakaj

  DOI：10.1016/s0008-6215(02)00005-8

  日期：2002.3

  The transglucosidations of methyl 4-0-methyl-alpha- and -beta-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-0-methyl-alpha- and -beta-D-glueopyranoside in methanolic camphor-10-sutfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product ( approximate to 59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side. (C) 2002 Published by Elsevier Science Ltd.