2-acetyloxy-1-<(acetyloxy)methyl>ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 55728-59-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetyloxy-1-<(acetyloxy)methyl>ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol；1,3-di-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)glycerol；(β,β'-diacetoxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside)；(β,β'-Diacetoxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranosid)；(1,3-Diacetoxy-prop-2-yl)-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(1,3-diacetyloxypropan-2-yloxy)oxan-2-yl]methyl acetate
• CAS: 55728-59-1
• 化学式: C₂₁H₃₀O₁₄
• 分子量: 506.461
• InChiKey: UKYVGQJPUFNXKS-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-acetyloxy-1-<(acetyloxy)methyl>ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 吡啶 、 水 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 29.0h， 生成 (2R)-1-O-acetyl-3-O-trityl-2-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)glycerol
  参考文献：
  名称：

  Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols

  摘要：

  2-O-(beta-D-Glucopyranosyl) glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) lipases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.

  DOI：

  10.1016/0957-4166(94)80181-9
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 2-acetyloxy-1-<(acetyloxy)methyl>ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  A Simple Synthesis of Glucosyl Glycerols

  摘要：

  Beta-D-glucopyranosides, linked to C-2 or C-3 of the glycerol aglicone moiety, were unambiguously synthesized.

  DOI：

  10.1080/00397919408010167

文献信息

• Carter, Chemische Berichte, 1930, vol. 63, p. 1684,1687
  作者：Carter

  DOI：——

  日期：——