[(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] acetate | 720694-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] acetate
• CAS: 720694-42-8
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: OENROGJQPVUBCV-RECBEJSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] acetate 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (1R,2S,4R,5S,6R)-2-Allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol
  参考文献：
  名称：

  First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate

  摘要：

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.065
• 作为产物：
  描述：

  原乙酸三甲酯 、 乙酸酐 、 allyl α-D-isopropylidene-α-D-fucopyranoside 在 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 吡啶 为溶剂， 以58%的产率得到[(2R,3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] acetate
  参考文献：
  名称：

  First preparative synthesis of a 3-acetamido-3,6-dideoxy-d-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate

  摘要：

  The preparative synthesis of a 3 -acetamido- 3,6-dideoxy -D-galactopyranose N-phenyl-trifluoroacetimidate donor has been accomplished using as key step a silica gel mediated cyclization of an epoxytrichloroacetimidate, while other more conventional routes to aminosugars failed. Test glycosylations with the N-phenyl-trifluoroacetimidate donor are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.065