ethyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α-L-erythrohex-2-enopyranoside | 63764-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α-L-erythrohex-2-enopyranoside
• 英文别名: Aethyl-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid
• CAS: 63764-65-8；67425-05-2；102727-67-3
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: FAUMTXZOVRGAHC-FXBDTBDDSA-N

物化性质

• 沸点：
  258.5±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙醇 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 sulfonic polystyrene type resin 作用下， 以89 %的产率得到ethyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α-L-erythrohex-2-enopyranoside
  参考文献：
  名称：

  全氟溶剂辅助的酸催化立体控制 Ferrier 型糖基化

  摘要：

  本文描述的是全氟化溶剂在通过乙酰化糖醛的费里尔重排发生的O-/S-糖苷键的立体选择性形成中的首次应用。在该系统中，全氟正己烷和底物之间的弱相互作用可以增强反应性和立体控制。转化的启动仅需要极低的树脂-H +负载，并且温和的条件能够容纳广谱的糖供体和受体。这种化学物质的“绿色”特征体现在培养基的低毒性和易于回收以及产品分离操作的简单性。

  DOI：

  10.3390/molecules27217234

文献信息

• RuCl3·3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.09.061

  日期：2013.11

  By using RuCl3 center dot 3H(2)O as catalyst, an improved method for the synthesis of 2,3-unsaturated-glycosides has been established. A series of 2, 3-unsaturated-glucosides were obtained from 2,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-6-deoxy-L-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals
  作者：Peiran Chen、Dalin Zhang

  DOI：10.1016/j.tet.2014.09.060

  日期：2014.11

  By using Sm(OTf)(3) as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-L-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-L-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. (C) 2014 Elsevier Ltd. All rights reserved.
• Allylic rearrangement of 6-deoxyglycals having practical utility
  作者：Prakash Bhaté、Derek Horton、Waldemar Priebe

  DOI：10.1016/s0008-6215(00)90681-5

  日期：1985.12