(9H-fluoren-9-yl)methyl benzyl((2R,3R,4R,5R,6R)-3,4,5,7-tetrakis(benzyloxy)-6-hydroxy-1-oxoheptan-2-yl)carbamate | 1187830-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (9H-fluoren-9-yl)methyl benzyl((2R,3R,4R,5R,6R)-3,4,5,7-tetrakis(benzyloxy)-6-hydroxy-1-oxoheptan-2-yl)carbamate
• CAS: 1187830-23-4
• 化学式: C₅₇H₅₅NO₈
• 分子量: 882.066
• InChiKey: FZPLJRRHYCNEND-VJEAPBBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.34
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  103.76
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (9H-fluoren-9-yl)methyl benzyl((2R,3R,4R,5R,6R)-3,4,5,7-tetrakis(benzyloxy)-6-hydroxy-1-oxoheptan-2-yl)carbamate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以84%的产率得到9H-fluoren-9-ylmethyl N-benzyl-N-[(2R,3R,4R,5R,6R,7R)-2-methoxy-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)oxepan-3-yl]carbamate
  参考文献：
  名称：

  Access to Ring-Expanded Analogues of 2-Amino Sugars

  摘要：

  Ring-expanded 2-N-acetylamino sugar analogs Of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted (x-amino aldehyde intermediates made them central to the approach, First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.

  DOI：

  10.1021/ol9018387
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl benzyl((3S,4R,5R,6R,7R)-4,5,6,8-tetrakis(benzyloxy)-7-hydroxyoct-1-en-3-yl)carbamate 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到(9H-fluoren-9-yl)methyl benzyl((2R,3R,4R,5R,6R)-3,4,5,7-tetrakis(benzyloxy)-6-hydroxy-1-oxoheptan-2-yl)carbamate
  参考文献：
  名称：

  Access to Ring-Expanded Analogues of 2-Amino Sugars

  摘要：

  Ring-expanded 2-N-acetylamino sugar analogs Of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted (x-amino aldehyde intermediates made them central to the approach, First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.

  DOI：

  10.1021/ol9018387