(4aR,6R,8aS)-6-isopropoxy-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine | 1145681-77-1

• 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: (4aR,6R,8aS)-6-isopropoxy-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• 英文别名: 2-propyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS: 1145681-77-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: AROSMFIVARGCPM-ZJIFWQFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  、 异丙醇 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,1'-bis(di-tertbutylphosphino)ferrocene 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以68%的产率得到(4aR,6R,8aS)-6-isopropoxy-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Stereocontrolled O-Glycosylation with Palladium-Catalyzed Decarboxylative Allylation

  摘要：

  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.

  DOI：

  10.1021/jo502078c

文献信息

• Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives
  作者：Yuhya Watanabe、Tsubasa Itoh、Tohru Sakakibara

  DOI：10.1016/j.carres.2008.12.015

  日期：2009.3

  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.