phenyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-1-thio-β-D-glucopyranoside | 1169827-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyl-5-(thiophen-2-ylmethoxy)oxane
• CAS: 1169827-75-1
• 化学式: C₃₈H₃₈O₅S₂
• 分子量: 638.849
• InChiKey: WAAVTEYNJOFLIX-HRTJLHCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranose 、 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranose
  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
• 作为产物：
  描述：

  2-溴甲基噻吩 、 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以78%的产率得到phenyl 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-1-thio-β-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.