methyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranoside | 1169827-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-(thiophen-2-ylmethoxy)oxane
• CAS: 1169827-82-0
• 化学式: C₃₃H₃₆O₆S
• 分子量: 560.711
• InChiKey: LYBSWZLSJVMHQP-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 O-(3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-D-glucopyranosyl)trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranoside 、 methyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion

  摘要：

  The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective alpha-glucosylation of a trichloroacetimidate donor: increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.018

文献信息

• Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion
  作者：Daniel J. Cox、Antony J. Fairbanks

  DOI：10.1016/j.tetasy.2009.02.018

  日期：2009.5

  The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective alpha-glucosylation of a trichloroacetimidate donor: increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor. (C) 2009 Elsevier Ltd. All rights reserved.