3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 1169827-85-3

• 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->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• CAS: 1169827-85-3
• 化学式: C₅₃H₅₆O₁₁S
• 分子量: 901.087
• InChiKey: XOAIIFBILIQFOF-LNFVWCMVSA-N

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 、 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到3,4,6-tri-O-benzyl-2-O-(thiophen-2-ylmethyl)-α-D-glucopyranosyl-(1->3)-methyl-2-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