allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 1392399-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 1392399-41-5
• 化学式: C₂₉H₄₀O₁₈
• 分子量: 676.626
• InChiKey: XRDJENZJYZRSNB-IREMCPGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  烯丙醇 、 β-D-maltose octaacetate 在 三氟化硼乙醚 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以18%的产率得到allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  A high-yielding synthesis of allyl glycosides from peracetylated glycosyl donors

  摘要：

  beta-Configured peracetylated sugars are often used as easily accessible glycosyl donors that are typically activated with common Lewis acids such as boron trifluoride or trimethylsilyltrifluoromethane sulfonate. Often these glycosylations occur with unsatisfactory yields due to incomplete reactions or extensive byproduct formation, primarily as a result of loss of an additional acetyl group generating partially unprotected glycosides. Here we report a simple glycosylation-reacetylation protocol for the generation of predominantly beta-configured peracetylated allyl glucoside, -galactoside, -lactoside, and -maltoside with substantially improved reaction yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.05.008