methoxycarbonylmethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside | 441017-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxycarbonylmethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• 英文别名: methyl 2-[(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]sulfanylacetate
• CAS: 441017-65-8
• 化学式: C₃₀H₃₄O₇S
• 分子量: 538.662
• InChiKey: DEOAFZWBGAUHQT-LXRLAABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methoxycarbonylmethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 在 甲醇 、 4 A molecular sieve 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 methoxycarbonylmethyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Solution-Phase Hexasaccharide Synthesis Using Glucosyl Iodides

  摘要：

  [GRAPHIC]Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the a-glycosides as the only isolated products in yields ranging from 84% to 94%. Oligomer synthesis can take place in an iterative 1 + 1 + 1 fashion or in a convergent manner where dimer iodides serve as donors for higher order acceptors.

  DOI：

  10.1021/ol025887d
• 作为产物：
  描述：

  acetyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 methoxycarbonylmethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Lam, Son N.; Gervay-Hague, Jacquelyn, Carbohydrate Research, 2002, vol. 337, # 21-23, p. 1952 - 1966

  摘要：

  DOI：

文献信息

• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.