methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3,3-difluoro-α-D-ribo-hexopyranoside | 134110-39-7

• 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: methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3,3-difluoro-α-D-ribo-hexopyranoside
• 英文别名: (2R,4aR,6S,7S,8aR)-8,8-difluoro-6-methoxy-2-phenyl-7-phenylmethoxy-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxine
• CAS: 134110-39-7
• 化学式: C₂₁H₂₂F₂O₅
• 分子量: 392.399
• InChiKey: ZNBBSERYWCZQMT-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3,3-difluoro-α-D-ribo-hexopyranoside 在 盐酸 、 硫酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 41.5h， 生成
  参考文献：
  名称：

  Synthesis of 2-deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose. A formal synthesis of gemcitabine

  摘要：

  The title compound 2-Deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose (17), was synthesised from D-glucose and from D-mannose. The key steps of the synthesis from D-glucose are obtaining the 3,3-difluoropyranose 9 by reacting the ulose 7 with DAST. and their conversion into the difluorofuranoside 17 by a degradative reaction of diol 16. Starting from D-mannose the synthesis obtains the 3,3-difluoroglycal 22 by reaction of the ulose 18 with DAST and oxidation-elimination of selenoglycoside 21. Ozonolysis of 22 gives the difluorofuranose 17. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00086-6
• 作为产物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 在 二乙胺基三氟化硫 作用下， 以 苯 为溶剂， 反应 10.0h， 以48%的产率得到methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3,3-difluoro-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  gem-Difluorination versus 1,2-migration and fragmentation in the reaction of 2- and 3-uloses with DAST. Influence of stereochemistry at the anomeric carbon atom

  摘要：

  DOI：

  10.1021/jo00014a047

文献信息

• gem-Difluorination versus 1,2-migration and fragmentation in the reaction of 2- and 3-uloses with DAST. Influence of stereochemistry at the anomeric carbon atom
  作者：Anas El-Laghdagh、Raouf Echarri、M. Isabel Matheu、M. Isabel Barrena、Sergio Castillon、Jordi Garcia

  DOI：10.1021/jo00014a047

  日期：1991.7
• Synthesis of 2-deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose. A formal synthesis of gemcitabine
  作者：Raül Fernández、M. Isabel Matheu、Raouf Echarri、Sergio Castillón

  DOI：10.1016/s0040-4020(98)00086-6

  日期：1998.4

  The title compound 2-Deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose (17), was synthesised from D-glucose and from D-mannose. The key steps of the synthesis from D-glucose are obtaining the 3,3-difluoropyranose 9 by reacting the ulose 7 with DAST. and their conversion into the difluorofuranoside 17 by a degradative reaction of diol 16. Starting from D-mannose the synthesis obtains the 3,3-difluoroglycal 22 by reaction of the ulose 18 with DAST and oxidation-elimination of selenoglycoside 21. Ozonolysis of 22 gives the difluorofuranose 17. (C) 1998 Elsevier Science Ltd. All rights reserved.