4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3-E-butene-1,2(S)-di-O-acetate | 918334-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3-E-butene-1,2(S)-di-O-acetate
• 英文别名: [(E,2S)-2-acetyloxy-4-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]but-3-enyl] acetate
• CAS: 918334-60-8
• 化学式: C₄₂H₄₆O₉
• 分子量: 694.822
• InChiKey: RJFBEVIFDFOISA-AUAKCKIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  51
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3-E-butene-1,2(S)-di-O-acetate 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.67h， 生成 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-2(S)-O-stearoyl-3-E-butene
  参考文献：
  名称：

  Efficient Synthesis of a C-Analogue of the Immunogenic Bacterial Glycolipid BbGL2

  摘要：

  Synthesis of a C-analogue of bacterial glycolipid BbGL2 is reported using Grignard reaction of in situ generated beta-galactosyl iodide and subsequent olefin cross metathesis reaction of C-vinyl galactoside as key steps.

  DOI：

  10.1021/ol062354m
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 碘代三甲硅烷 、 硫酸 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 107.08h， 生成 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3-E-butene-1,2(S)-di-O-acetate
  参考文献：
  名称：

  Efficient Synthesis of a C-Analogue of the Immunogenic Bacterial Glycolipid BbGL2

  摘要：

  Synthesis of a C-analogue of bacterial glycolipid BbGL2 is reported using Grignard reaction of in situ generated beta-galactosyl iodide and subsequent olefin cross metathesis reaction of C-vinyl galactoside as key steps.

  DOI：

  10.1021/ol062354m

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.