methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside | 149057-38-5

• 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 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside
• 英文别名: (4aR,6S,7R,8R,8aS)-7-fluoro-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 149057-38-5
• 化学式: C₁₄H₁₇FO₅
• 分子量: 284.284
• InChiKey: KGDKZXWLTPVXED-ZWVDJKGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside 在 barium sulfate 、 钯 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙酸乙酯 、 苯 为溶剂， 反应 3.0h， 生成 methyl 2,6-dideoxy-2-fluoro-β-L-talopyranoside
  参考文献：
  名称：

  A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-l-talopyranoside

  摘要：

  The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-alpha,beta-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-alpha-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00325-5
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α,β-D-ribo-hexopyranosid-3-ulose 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以42%的产率得到methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside
  参考文献：
  名称：

  A concise synthesis of methyl 2,6-dideoxy-2-fluoro-β-l-talopyranoside

  摘要：

  The 4,6-benzylidene acetal of methyl 2-deoxy-2-fluoro-alpha,beta-D-glucopyranoside underwent inversion at C-3 via an oxidation-reduction sequence, and treatment of the derived 3-acetate with N-bromosuccinimide in carbon tetrachloride gave methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-alpha-D-allopyranoside (6). Dehydrobromination of 6 and reduction of the resultant 5,6-ene gave the 5-epimer of 6, which after removal of the ester substituents, afforded the title compound in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00325-5