allyl 2-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside
• 英文别名: Allyl 2-O-benzoyl-3-O-benzyl-alpha-L-rhamnopyranoside；[(2R,3R,4R,5S,6S)-5-hydroxy-6-methyl-4-phenylmethoxy-2-prop-2-enoxyoxan-3-yl] benzoate
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: YJCAPLCOTDGLOK-PBRHZFIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 烯丙基 3-O-苄基-alpha-L-吡喃鼠李糖苷 在 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以78%的产率得到allyl 2-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

  摘要：

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.001

文献信息

• Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D
  作者：Qian Yang、Ming Lei、Qin-Jian Yin、Jin-Song Yang

  DOI：10.1016/j.carres.2007.03.001

  日期：2007.7

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.