[(2R,3R,4S,5R,6Z)-3,4,5-triacetyloxy-6-prop-2-enylideneoxan-2-yl]methyl acetate | 199738-53-9

• 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: [(2R,3R,4S,5R,6Z)-3,4,5-triacetyloxy-6-prop-2-enylideneoxan-2-yl]methyl acetate
• CAS: 199738-53-9
• 化学式: C₁₇H₂₂O₉
• 分子量: 370.356
• InChiKey: SCVPNJHFAZMQPC-NWZDRVGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6Z)-3,4,5-triacetyloxy-6-prop-2-enylideneoxan-2-yl]methyl acetate 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 (2R,3S,4S,5R,6Z)-2-(hydroxymethyl)-6-prop-2-enylideneoxane-3,4,5-triol
  参考文献：
  名称：

  A stereocontrolled radical access to C-allyl β-D-glycopyranosides from glycopyranosylidene dihalides found en route to C-glycodienes

  摘要：

  Application of the Keck reaction to peracetylated glycopyranosylidene dihalides under mild conditions led efficiently to chloro C-allyl glycosides which were converted to either the corresponding C-allyl beta-D-glycosides or C-D-glycodienes on treatment with, respectively, tri-n-butyltin hydride and DBU. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10215-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride 在 偶氮二异丁腈 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 、 苯 为溶剂， 反应 2.33h， 生成 [(2R,3R,4S,5R,6Z)-3,4,5-triacetyloxy-6-prop-2-enylideneoxan-2-yl]methyl acetate
  参考文献：
  名称：

  A stereocontrolled radical access to C-allyl β-D-glycopyranosides from glycopyranosylidene dihalides found en route to C-glycodienes

  摘要：

  Application of the Keck reaction to peracetylated glycopyranosylidene dihalides under mild conditions led efficiently to chloro C-allyl glycosides which were converted to either the corresponding C-allyl beta-D-glycosides or C-D-glycodienes on treatment with, respectively, tri-n-butyltin hydride and DBU. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10215-5

文献信息

• Expeditious synthesis of C-glycosyl conjugated dienes and aldehydes from sugar lactones
  作者：Wen-Bin Yang、Chuan-Fa Chang、Shwu-Huey Wang、Chin-Fen Teo、Chun-Hung Lin

  DOI：10.1016/s0040-4039(01)00814-0

  日期：2001.7

  Several C-glycosyl conjugated dienes were prepared in two steps from protected sugar lactones via addition of allylmagnesium chloride and the subsequent dehydration. A sequence of allylic addition, ozonolysis and dehydration led to the corresponding glycosyl conjugated aldehydes. These conjugated functionalities can be used as diagnostic chromophores for sugar synthesis and purification. The synthetic

  通过添加烯丙基氯化镁并随后进行脱水，由受保护的糖内酯分两步制备几种C-糖基共轭二烯。一系列烯丙基加成，臭氧分解和脱水导致相应的糖基缀合的醛。这些共轭的功能可以用作糖合成和纯化的诊断生色团。还进行了糖基二烯的合成研究。糖二烯的氢硼化取决于后处理条件而导致均一醇或螺缩醛。