Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside | 182167-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside
• CAS: 182167-87-9
• 化学式: C₃₆H₃₈O₁₂
• 分子量: 662.691
• InChiKey: OYQQWZCIYKEJJM-OJHOVPSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  156.28
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以84%的产率得到Allyl 3-O-(3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-D-mannopyranoside 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684