3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranosylfluoride | 1169827-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranosylfluoride
• 英文别名: (2S,3R,4S,5R,6R)-2-fluoro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-(thiophen-2-ylmethoxy)oxane
• CAS: 1169827-74-0
• 化学式: C₃₂H₃₃FO₅S
• 分子量: 548.675
• InChiKey: BCHHQBGRRYVLRR-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranosylfluoride 、 双丙酮半乳糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,4,6-tri-O-benzyl-2-O-(thiophen-2-yl)-β-D-glucopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 3,4,6-tri-O-benzyl-2-O-(thiophen-2-yl)-α-D-glucopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-D-galactopyranose
  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 、 3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以74%的产率得到3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-β-D-glucopyranosylfluoride
  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.