3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranosyl-(1->2)-methyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 1169827-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranosyl-(1->2)-methyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: (2R,4aR,6S,7S,8S,8aR)-7-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-(thiophen-2-ylmethoxy)oxan-2-yl]oxy-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 1169827-83-1
• 化学式: C₅₃H₅₆O₁₁S
• 分子量: 901.087
• InChiKey: DOQIMCSXBCDEAQ-LNFVWCMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  O-(3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-D-glucopyranosyl)trichloroacetimidate 、 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranosyl-(1->2)-methyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  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.