octyl 4,6-O-benzylidene-β-D-glucopyranoside | 118249-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-6-octoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 118249-73-3
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: CBYZDFQCAFRHGO-UCGFNCKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octyl 4,6-O-benzylidene-β-D-glucopyranoside 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以67%的产率得到octyl 4,6-O-benzylidene-β-D-erythro-2,3-dideoxyhex-2-enopyranoside
  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：

  苯甲醛二甲缩醛 、 n-辛基-β-D-吡喃葡萄糖苷 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以100%的产率得到octyl 4,6-O-benzylidene-β-D-glucopyranoside
  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

• Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside
  作者：David Rabuka、Ole Hindsgaul

  DOI：10.1016/s0008-6215(02)00178-7

  日期：2002.11

  All six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside have been chemically synthesized and characterized by high-resolution H-1, C-13 and P-31 NMR spectroscopy. Phosphorylation causes characteristic downfield shifts of the nucleus at the substituted site in the H-1 and C-13 NMR signals and resulted in a unique P-31 signal for each compound. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereospecific synthesis of β-d-allopyranosides by dihydroxylation of β-d-erythro-2,3-dideoxyhex-2-enopyranosides
  作者：Paul V Murphy、Julie L O'Brien、Amos B Smith

  DOI：10.1016/s0008-6215(01)00181-1

  日期：2001.9

  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.