5-Azido-2,3-cyclohexylidene-5-deoxy-D-ribono-1,4-lactone | 28277-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Azido-2,3-cyclohexylidene-5-deoxy-D-ribono-1,4-lactone
• CAS: 28277-84-1
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: JNONKIDOLNKIEP-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-Azido-2,3-cyclohexylidene-5-deoxy-D-ribono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、150.0 kPa 条件下， 反应 2.0h， 以94%的产率得到5-Amino-2,3-O-cyclohexylidene-5-deoxy-D-ribono-1,5-lactam
  参考文献：
  名称：

  Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation

  摘要：

  The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)(5) and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)(5)-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is p-selective and has been applied further to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<691::aid-chem691>3.0.co;2-e
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 sodium azide 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 5-Azido-2,3-cyclohexylidene-5-deoxy-D-ribono-1,4-lactone
  参考文献：
  名称：

  Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation

  摘要：

  The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)(5) and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)(5)-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is p-selective and has been applied further to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<691::aid-chem691>3.0.co;2-e

文献信息

• Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation
  作者：Karl Heinz Dötz、Markus Klumpe、Martin Nieger

  DOI：10.1002/(sici)1521-3765(19990201)5:2<691::aid-chem691>3.0.co;2-e

  日期：1999.2.1

  The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)(5) and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)(5)-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is p-selective and has been applied further to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate.