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 | 1187830-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 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
• CAS: 1187830-28-9
• 化学式: C₅₈H₅₇NO₈
• 分子量: 896.092
• InChiKey: LVCPELDIPVHMBF-JVODKBMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  67
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 二乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以80%的产率得到(2R,3R,4R,5R,6R,7R)-N-benzyl-4,5,6-tris(benzyloxy)-7-((benzyloxy)methyl)-2-methoxyoxepan-3-amine
  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：

  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