1,4-anhydro-3,6-di-O-benzyl-2-deoxy-β-D-lyxo-hexopyranose | 185803-67-2

• 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: 1,4-anhydro-3,6-di-O-benzyl-2-deoxy-β-D-lyxo-hexopyranose
• 英文别名: (1S,3R,4R,5R)-5-phenylmethoxy-3-(phenylmethoxymethyl)-2,7-dioxabicyclo[2.2.1]heptane
• CAS: 185803-67-2
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: QYCMDIMRAKHYPP-YSTOQKLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-3,6-di-O-benzyl-2-deoxy-β-D-lyxo-hexopyranose 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 5.0h， 生成 (E)-2,5-anhydro-4,7-di-O-benzyl-1,3-dideoxy-1-C-phenyl-D-lyxo-hept-1-enitol
  参考文献：
  名称：

  Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal

  摘要：

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00480-9
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-6-O-pivaloyl-β-D-lyxo-hexopyranose 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1,4-anhydro-3,6-di-O-benzyl-2-deoxy-β-D-lyxo-hexopyranose
  参考文献：
  名称：

  Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal

  摘要：

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00480-9

文献信息

• Stereocontrolled synthesis of O- and C-furanosides through 1,4-iodocyclisation of d-galactal
  作者：Véronique Jaouen、Anne Jégou、Lénaïck Lemée、Alain Veyrières

  DOI：10.1016/s0040-4020(99)00480-9

  日期：1999.7

  Iodocyclisation of 6-O-protected-D-galactal, followed by radical reduction, gives [2.2.1] bicyclic acetals which are regioselectively opened by various nucleophiles (alcohols, allyltrimethylsilane, triphenylphosphine) to give furanosyl compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.