2,5-anhydro-3-azido-3,4-dideoxy-1,4-difluoro-1-O-methyl-D-talitol | 676265-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2,5-anhydro-3-azido-3,4-dideoxy-1,4-difluoro-1-O-methyl-D-talitol
• CAS: 676265-78-4
• 化学式: C₇H₁₁F₂N₃O₃
• 分子量: 223.179
• InChiKey: UMDZQCVXLJOJLB-KRWZAIJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 2,5-anhydro-3-azido-3,4-dideoxy-1,4-difluoro-1-O-methyl-D-talitol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以69%的产率得到2,5-anhydro-3-azido-6-O-tert-butyl-diphenylsilyl-3,4-dideoxy-1,4-difluoro-1-O-methyl-D-talitol
  参考文献：
  名称：

  Fluorination of 2-hydroxy-hexopyranosides by DAST: towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides

  摘要：

  Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-I-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. F-19/H-1 and F-19/C-13 coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O-methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.034
• 作为产物：
  描述：

  methyl 3-azido-4,6-O-benzylidene-3-deoxy-β-D-glucopyranoside 在 二乙胺基三氟化硫 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以40%的产率得到3-azido-4,6-O-benzylidene-3-deoxy-2-O-methyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Fluorination of 2-hydroxy-hexopyranosides by DAST: towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides

  摘要：

  Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-I-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. F-19/H-1 and F-19/C-13 coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O-methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.034