phenyl 2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside | 1312425-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside
• CAS: 1312425-23-2
• 化学式: C₁₈H₂₂O₈S
• 分子量: 398.434
• InChiKey: BVRVOLPKYWYKNO-MDMSPXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside 、 2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖 三氯乙酰亚胺酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以85%的产率得到phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Four-component one-pot synthesis of a branched manno-pentasaccharide: tert-butyldiphenylsilyl ether as an in situ removable carbohydrate-protecting group

  摘要：

  A branched mannose-pentasaccharide was synthesized in a convergent one-pot sequence involving chemo- and regioselective glycosylations of suitable acceptors and in situ removal of tert-butyldiphenylsilyl group. The process demonstrated that a combination of TMSOTf and TfOH can be used as an effective reagent for the fast and selective in situ de-protection of tert-butyldiphenylsilyl group, and also serve as part of the promoter system for the subsequent glycosylation reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.109
• 作为产物：
  描述：

  苯基1-硫代吡喃己糖苷 、 乙酰氯 在 对甲苯磺酸 、 原甲酸三甲酯 、 溶剂黄146 、 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.92h， 以30%的产率得到phenyl 2,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Four-component one-pot synthesis of a branched manno-pentasaccharide: tert-butyldiphenylsilyl ether as an in situ removable carbohydrate-protecting group

  摘要：

  A branched mannose-pentasaccharide was synthesized in a convergent one-pot sequence involving chemo- and regioselective glycosylations of suitable acceptors and in situ removal of tert-butyldiphenylsilyl group. The process demonstrated that a combination of TMSOTf and TfOH can be used as an effective reagent for the fast and selective in situ de-protection of tert-butyldiphenylsilyl group, and also serve as part of the promoter system for the subsequent glycosylation reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.109

文献信息

• Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides
  作者：Samrat Dutta、Swarbhanu Sarkar、Shyam Ji Gupta、Asish Kumar Sen

  DOI：10.1016/j.tetlet.2012.11.101

  日期：2013.2

  A novel and high yielding glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and iodine as promoter is described. The donors are stable and can be chemoselectively activated in the presence of thioethyl and thiophenyl glycosides. The application of this methodology in one-pot consecutive glycosylation reaction is described. (C) 2012 Elsevier Ltd. All rights reserved.