1,5,6-trideoxy-1-methylidene-3,4-di-O-benzyl-5-ene-D-glucofuranose | 607403-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5,6-trideoxy-1-methylidene-3,4-di-O-benzyl-5-ene-D-glucofuranose
• 英文别名: 3,4-O-dibenzyl-2-methylene-5-vinyl tetrahydrofuran；(2R,3S,4R)-2-ethenyl-5-methylidene-3,4-bis(phenylmethoxy)oxolane
• CAS: 607403-63-4
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: IVQOTIRBLGCHHL-HKBOAZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5,6-trideoxy-1-methylidene-3,4-di-O-benzyl-5-ene-D-glucofuranose 在 palladium on activated charcoal 氢气 、 三异丁基铝 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0~80.0 ℃ 、379.21 kPa 条件下， 生成 (1S,3S)-1,2,3-环庚烷三醇
  参考文献：
  名称：

  Highly stereoselective synthesis of a seven-membered carbasugar via triisobutylaluminium promoted Claisen rearrangement

  摘要：

  2-Methylene-5-vinyl-tetrahydrofuran derivative 6 was obtained from alpha-D-glucose. Treatment of 6 with triisobutylaluminium (TIBAL) induced Claisen expansion reaction to give the seven-membered carbasugar derivative 7, which represents a new type of chiral building blocks. The rearrangement reaction has been proved to be highly stereoselective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00490-7
• 作为产物：
  描述：

  2,3-di-O-benzyl-5,6-dideoxy-5-ene-D-glucofuranose 在 吡啶 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,5,6-trideoxy-1-methylidene-3,4-di-O-benzyl-5-ene-D-glucofuranose
  参考文献：
  名称：

  Highly stereoselective synthesis of a seven-membered carbasugar via triisobutylaluminium promoted Claisen rearrangement

  摘要：

  2-Methylene-5-vinyl-tetrahydrofuran derivative 6 was obtained from alpha-D-glucose. Treatment of 6 with triisobutylaluminium (TIBAL) induced Claisen expansion reaction to give the seven-membered carbasugar derivative 7, which represents a new type of chiral building blocks. The rearrangement reaction has been proved to be highly stereoselective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00490-7