methyl 4,6-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-D-erythro-hexopyranoside | 205592-62-7

• 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: methyl 4,6-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-D-erythro-hexopyranoside
• 英文别名: [(2R,3R,6S)-3-benzoyloxy-4,4-difluoro-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 205592-62-7
• 化学式: C₂₁H₂₀F₂O₆
• 分子量: 406.383
• InChiKey: XEJADILXXQBLCR-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-D-erythro-hexopyranoside 在 三氟甲磺酸三甲基硅酯 、 硫酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.75h， 生成 4-N-acetyl-1-(4',6'-di-O-benzoyl-2',3'-dideoxy-3',3'-difluoro-α-D-erythro-hexopyranosyl)cytosine
  参考文献：
  名称：

  吉西他滨2'，3'-二脱氧-3'，3'-二氟和2'，3'-二脱氧-2'，2'-二氟-吡喃糖基核苷类似物的合成

  摘要：

  所述宝石-difluoronucleosides 1和2，吉西他滨的吡喃糖类似物，已经从d-甘露糖和d葡萄糖分别合成。关键步骤是通过相应的蔗糖与DAST反应形成二氟亚甲基，并进行糖基化。

  DOI：

  10.1016/s0040-4020(99)00468-8
• 作为产物：
  描述：

  methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 在 盐酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 methyl 4,6-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-D-erythro-hexopyranoside
  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

文献信息

• 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.
• Synthesis of 2′,3′-dideoxy-3′,3′-difluoro and 2′,3′-dideoxy-2′,2′-difluoro-pyranosyl nucleosides analogues of gemcitabine
  作者：Raul Fernández、Sergio Castillón

  DOI：10.1016/s0040-4020(99)00468-8

  日期：1999.7

  The gem-difluoronucleosides 1 and 2, pyranosyl analogues of gemcitabine, have been synthesized from d-mannose and d-glucose respectively. The key steps were the formation of the difluoromethylene group by reaction of the corresponding ulose with DAST, and the glycosylation.

  所述宝石-difluoronucleosides 1和2，吉西他滨的吡喃糖类似物，已经从d-甘露糖和d葡萄糖分别合成。关键步骤是通过相应的蔗糖与DAST反应形成二氟亚甲基，并进行糖基化。