tert-butyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside | 1145681-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: tert-butyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS: 1145681-79-3
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: QMUCUDRGLKJMKM-XUWVNRHRSA-N

物化性质

• 沸点：
  398.7±42.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  、 叔丁醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 、 tert-butyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives

  摘要：

  The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an a anomer with high stereoselectivity. We have found that 3-O-mesyl-D-glycals 2-4 were smoothly reacted with alcohols in the presence of triethylamine. The present reaction was shown to proceed under kinetic control to give similar to 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.015

文献信息

• Stereocontrolled <i>O</i>-Glycosylation with Palladium-Catalyzed Decarboxylative Allylation
  作者：Shaohua Xiang、Jingxi He、Yu Jia Tan、Xue-Wei Liu

  DOI：10.1021/jo502078c

  日期：2014.12.5

  The Pd-pi-allyl intermediate in an electron-rich glycal system with poor reactivity is employed as an efficient glycosyl donor. Starting from glucal derived carbonate, various O-glycosides were formed via a palladium-catalyzed reaction through a tandem decarboxylation, proton abstraction, and nucleophilic addition, in good yields with excellent selectivity. Iterative glycosylation with the same strategy may provide an access to complex oligosaccharides.