methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-D-threo-hex-5-eno-pyranoside | 825632-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-D-threo-hex-5-eno-pyranoside
• 英文别名: [(3S,4R,6R)-4-azido-6-methoxy-2-methylideneoxan-3-yl] acetate
• CAS: 825632-37-9
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: HNHMRCLDWVKWOL-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-D-threo-hex-5-eno-pyranoside 在 吡啶 、 sodium azide 、 硫酸 、 盐酸羟胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.25h， 生成 Z-(2R,3R,5R)-2,3-diazido-5-hydroxycyclohexanone oxime
  参考文献：
  名称：

  From Tri‐O‐Acetyl‐D‐Glucal to (2R,3R,5R)‐2,3‐Diazido‐5‐Hydroxycyclohexanone Oxime

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha/beta-D-arabino- and -alpha/beta-D-ribo-hexopyranosides were transformed into 6-iodo analogues via p-tolylsulfonyl compounds. Elimination of hydrogen iodide from 6-iodo glycosides provided methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides or 3-azido-4-O-p-tolylsulfonyl-2,3,6-trideoxy-alpha-D-threo- and -beta-D-erythro-hex-5-eno-pyranosides. Ferrier's carbocyclization of 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides gave (2S,3R,5R)-2-acetoxy-3-azido-5-hydroxycyclohcxanone, which was converted into oxime. The 2-OAc group in oxime was substituted by azide ion to yield (2R,3R,5R)-2,3-diazido-5-hydroxycyclohexanone oxime. The configuration and conformation of all products are widely discussed on the basis of the H-1 and C-13 NMR.

  DOI：

  10.1081/car-200040117
• 作为产物：
  描述：

  methyl 4-O-acetyl-3-azido-6-iodo-2,3,6-trideoxy-β-D-arabino-hexopyranoside 在 吡啶 、 silver fluoride 作用下， 反应 48.0h， 以72%的产率得到methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-D-threo-hex-5-eno-pyranoside
  参考文献：
  名称：

  From Tri‐O‐Acetyl‐D‐Glucal to (2R,3R,5R)‐2,3‐Diazido‐5‐Hydroxycyclohexanone Oxime

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha/beta-D-arabino- and -alpha/beta-D-ribo-hexopyranosides were transformed into 6-iodo analogues via p-tolylsulfonyl compounds. Elimination of hydrogen iodide from 6-iodo glycosides provided methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides or 3-azido-4-O-p-tolylsulfonyl-2,3,6-trideoxy-alpha-D-threo- and -beta-D-erythro-hex-5-eno-pyranosides. Ferrier's carbocyclization of 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides gave (2S,3R,5R)-2-acetoxy-3-azido-5-hydroxycyclohcxanone, which was converted into oxime. The 2-OAc group in oxime was substituted by azide ion to yield (2R,3R,5R)-2,3-diazido-5-hydroxycyclohexanone oxime. The configuration and conformation of all products are widely discussed on the basis of the H-1 and C-13 NMR.

  DOI：

  10.1081/car-200040117