methyl 3-azido-2,3-dideoxy-6-O-p-tolylsulfonyl-α-D-xylo-hexopyranoside | 844694-82-2

• 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-6-O-p-tolylsulfonyl-α-D-xylo-hexopyranoside
• 英文别名: [(2R,3R,4S,6S)-4-azido-3-hydroxy-6-methoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 844694-82-2
• 化学式: C₁₄H₁₉N₃O₆S
• 分子量: 357.387
• InChiKey: MCIHZOPWXRLFJB-RFQIPJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-6-O-p-tolylsulfonyl-α-D-xylo-hexopyranoside 在 吡啶 、 silver fluoride 、 sodium iodide 作用下， 以 吡啶 、 丙酮 为溶剂， 生成 methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-β-L-threo-hex-5-enopyranoside
  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-α-D-xylo-hexopyranoside 在 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 methyl 3-azido-2,3-dideoxy-6-O-p-tolylsulfonyl-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis, crystal structure, and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-α-d-xylo-hexopyranoside

  摘要：

  Synthesis of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl- and -6-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranosides is presented. High-resolution H-1 and C-13 NMR spectral data for both compounds and their precursors, and the single-crystal X-ray diffraction analysis for methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranoside are reported. The influence of the O-protective group on the chemical shift of adjacent atoms in the 1H and 13 C NMR spectra is discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.016

文献信息

• Synthesis, crystal structure, and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-α-d-xylo-hexopyranoside
  作者：Beata Liberek、Artur Sikorski、Antoni Konitz

  DOI：10.1016/j.carres.2004.10.016

  日期：2005.1

  Synthesis of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl- and -6-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranosides is presented. High-resolution H-1 and C-13 NMR spectral data for both compounds and their precursors, and the single-crystal X-ray diffraction analysis for methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranoside are reported. The influence of the O-protective group on the chemical shift of adjacent atoms in the 1H and 13 C NMR spectra is discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and conformational studies on methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-hex-5-enopyranosides of the l series
  作者：Beata Liberek

  DOI：10.1016/j.carres.2005.06.019

  日期：2005.9

  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.