methyl 3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside | 865093-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside
• 英文别名: (2R,3R,4S,6R)-4-azido-2-(hydroxymethyl)-6-methoxyoxan-3-ol
• CAS: 865093-42-1
• 化学式: C₇H₁₃N₃O₄
• 分子量: 203.198
• InChiKey: FLZWXHAJKPSXOG-BDVNFPICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107.68
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 methyl 3-azido-6-iodo-2,3,6-trideoxy-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the l series

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha-(D)-xylo-, -alpha-(D)-lyxo-, and -beta-(D)-xylo-hexopyranosides were converted into 4-O-acetyl-3azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-beta-(L)-erythro-, -alpha-(L)-threo-, and -beta-(L)-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of H-1 and C-13 NMR data. Factors determining conformational energy in 4- O-protected- 3 -azido-2,3,6,-trideoxy-hex-5-enopyrano sides are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.019
• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside 以96%的产率得到methyl 3-azido-2,3-dideoxy-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the l series

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha-(D)-xylo-, -alpha-(D)-lyxo-, and -beta-(D)-xylo-hexopyranosides were converted into 4-O-acetyl-3azido-6-iodo-2,3,6-trideoxy analogues via 6-O-p-tolylsulfonyl compounds. The elimination of hydrogen iodide from 6-iodo glycosides yielded methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-beta-(L)-erythro-, -alpha-(L)-threo-, and -beta-(L)-threo-hex-5-enopyranosides. The configuration and conformation of all products are evaluated in depth on the basis of H-1 and C-13 NMR data. Factors determining conformational energy in 4- O-protected- 3 -azido-2,3,6,-trideoxy-hex-5-enopyrano sides are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.019