benzyl 4,6-di-O-benzoyl-2-O-benzyl-3-deoxy-3,3-difluoro-α-D-gluco-pyranoside | 205592-59-2

• 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: benzyl 4,6-di-O-benzoyl-2-O-benzyl-3-deoxy-3,3-difluoro-α-D-gluco-pyranoside
• 英文别名: [(2R,3R,5S,6S)-3-benzoyloxy-4,4-difluoro-5,6-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 205592-59-2
• 化学式: C₃₄H₃₀F₂O₇
• 分子量: 588.605
• InChiKey: XYMBZGPFAQLPCU-BZBLMLCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 4,6-di-O-benzoyl-2-O-benzyl-3-deoxy-3,3-difluoro-α-D-gluco-pyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 [(2R,3R,5S,6R)-3-benzoyloxy-4,4-difluoro-5,6-dihydroxyoxan-2-yl]methyl benzoate 、 [(2R,3R,5S,6S)-3-benzoyloxy-4,4-difluoro-5,6-dihydroxyoxan-2-yl]methyl benzoate
  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：

  (2R,4aR,6S,7S,8aR)-6,7-Bis-benzyloxy-8,8-difluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 盐酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 benzyl 4,6-di-O-benzoyl-2-O-benzyl-3-deoxy-3,3-difluoro-α-D-gluco-pyranoside
  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