2,3,4-tri-O-acetyl-β-D-xylopyranosylamine | 82823-51-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-β-D-xylopyranosylamine
• 英文别名: Acetic acid (2R,3R,4R,5R)-3,5-diacetoxy-2-amino-tetrahydro-pyran-4-yl ester
• CAS: 82823-51-6
• 化学式: C₁₁H₁₇NO₇
• 分子量: 275.258
• InChiKey: GITCHZVOIYKCQI-GWOFURMSSA-N

物化性质

• 沸点：
  336.5±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  114.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-D-xylopyranosylamine 在 barium methoxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 N-(β-D-ribopyranosyl)propionamide
  参考文献：
  名称：

  Examination of the influence of C5-hydroxymethyl group and configurations of hydroxyl groups at C2, C3, and C4 stereocentres on the N-glycosidic torsion: synthesis and X-ray crystallographic investigation of N-(d-ribopyranosyl)alkanamides as N-glycoprotein linkage region analogs

  摘要：

  N-Linked glycosylation is not only present in eukaryotes but also occurs in archaea and bacteria and is mainly characterized by the beta-glucosylamine linkage to the asparagine (GlcNAc beta Asn). Earlier crystallographic studies aimed at understanding the structural significance of the linkage region constituents revealed that N-glycosidic torsion, phi(N) is influenced considerably by variation in the glycan part as compared to the aglycon moiety. The phi(N) value observed for Xyl beta NHAc deviated maximum as compared to that of the model compound, GlcNAc beta NHAc. The present work was undertaken to assess the influence of ribose on the N-glycosidic torsions and molecular assembly. Several ribopyranosyl alkanamides have been synthesized and crystal structures of three of them have been solved. A comprehensive crystal structure analysis of ribosyl alkanamides along with xylosyl and arabinosyl alkanamides showed the wide range of deviations in their phi(N) values as compared to the negligible deviation shown by hexopyranosyl alkanamides. This study revealed the importance of C5-hydroxymethyl group and hydroxyl group configurations at C2, C3, and C4 stereocentres in controlling the N-glycosidic torsions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.11.003
• 作为产物：
  描述：

  tetra-O-acetyl-D-ribopyranoside 在 叠氮基三甲基硅烷 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-acetyl-β-D-xylopyranosylamine
  参考文献：
  名称：

  Examination of the influence of C5-hydroxymethyl group and configurations of hydroxyl groups at C2, C3, and C4 stereocentres on the N-glycosidic torsion: synthesis and X-ray crystallographic investigation of N-(d-ribopyranosyl)alkanamides as N-glycoprotein linkage region analogs

  摘要：

  N-Linked glycosylation is not only present in eukaryotes but also occurs in archaea and bacteria and is mainly characterized by the beta-glucosylamine linkage to the asparagine (GlcNAc beta Asn). Earlier crystallographic studies aimed at understanding the structural significance of the linkage region constituents revealed that N-glycosidic torsion, phi(N) is influenced considerably by variation in the glycan part as compared to the aglycon moiety. The phi(N) value observed for Xyl beta NHAc deviated maximum as compared to that of the model compound, GlcNAc beta NHAc. The present work was undertaken to assess the influence of ribose on the N-glycosidic torsions and molecular assembly. Several ribopyranosyl alkanamides have been synthesized and crystal structures of three of them have been solved. A comprehensive crystal structure analysis of ribosyl alkanamides along with xylosyl and arabinosyl alkanamides showed the wide range of deviations in their phi(N) values as compared to the negligible deviation shown by hexopyranosyl alkanamides. This study revealed the importance of C5-hydroxymethyl group and hydroxyl group configurations at C2, C3, and C4 stereocentres in controlling the N-glycosidic torsions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.11.003

文献信息

• Ege, Guenter; Gilbert, Karlheinz; Heck, Reinhard, Angewandte Chemie, 1982, vol. 94, # 9, p. 715 - 716
  作者：Ege, Guenter、Gilbert, Karlheinz、Heck, Reinhard

  DOI：——

  日期：——