(4aR,6S,8aS)-2-(4-methoxyphenyl)-6-phenoxy-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine | 384343-32-2

• 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,6S,8aS)-2-(4-methoxyphenyl)-6-phenoxy-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• 英文别名: phenyl 4,6-O-benzylidene-β-D-erythro-2,3-dideoxyhex-2-enopyranoside
• CAS: 384343-32-2
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: WVANSLKRMQFYCK-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4aR,6S,8aS)-2-(4-methoxyphenyl)-6-phenoxy-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 在 三乙烯二胺 、 N-甲基吲哚酮 、 K₂OsO₂(H₂O)2 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以95%的产率得到phenyl 4,6-O-benzylidene-β-D-allopyranoside
  参考文献：
  名称：

  Stereospecific synthesis of β-d-allopyranosides by dihydroxylation of β-d-erythro-2,3-dideoxyhex-2-enopyranosides

  摘要：

  The synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00181-1
• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 咪唑 、 camphor-10-sulfonic acid 、 碘 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 (4aR,6S,8aS)-2-(4-methoxyphenyl)-6-phenoxy-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Stereospecific synthesis of β-d-allopyranosides by dihydroxylation of β-d-erythro-2,3-dideoxyhex-2-enopyranosides

  摘要：

  The synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00181-1

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.