2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 216862-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• CAS: 216862-40-7
• 化学式: C₅₅H₅₈O₁₁
• 分子量: 895.059
• InChiKey: IHHHSYRYEZHVEA-VIAGIRMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  66.0
• 可旋转键数：
  20.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 10% palladium on active carbon 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以94%的产率得到methyl 3-O-α-D-glucopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894
• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 在 2,4,6-三甲基吡啶 、 ammonium cerium(IV) nitrate 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 59.0h， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894

文献信息

• N-Iodosaccharin: A Potent New Activator of Thiophenylglycosides
  作者：M. Aloui、A. J. Fairbanks

  DOI：10.1055/s-2001-14612

  日期：——

  N-Iodosaccharin is found to be a potent activator of armed thiophenyl glycosides.

  研究发现，N-碘代糖精是一种能够有效激活带硫代苯糖苷的强效激活剂。
• Glycosylation Catalyzed by a Chiral Brønsted Acid
  作者：Daniel J. Cox、Martin D. Smith、Antony J. Fairbanks

  DOI：10.1021/ol1001895

  日期：2010.4.2

  The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochemical outcome of the glycosylation processes, hinting that perhaps diastereocontrol of glycosylation processes may become achievable through the judicious use of chiral organic catalysts.
• 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.