9H-fluoren-9-ylmethyl N-benzyl-N-[(2S,3S,4S,5R,6R,7R)-2-methoxy-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)oxepan-3-yl]carbamate | 1187830-26-7

• 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-[(2S,3S,4S,5R,6R,7R)-2-methoxy-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)oxepan-3-yl]carbamate
• CAS: 1187830-26-7
• 化学式: C₅₈H₅₇NO₈
• 分子量: 896.092
• InChiKey: LVCPELDIPVHMBF-RMGROAGESA-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-[(2S,3S,4S,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92%的产率得到(2S,3S,4S,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-ylmethyl N-benzyl-N-[(2S,3S,4R,5R,6R)-6-hydroxy-1-oxo-3,4,5,7-tetrakis(phenylmethoxy)heptan-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74%的产率得到9H-fluoren-9-ylmethyl N-benzyl-N-[(2S,3S,4S,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

文献信息

• Expanding the Scope of Aminosugars: Synthesis of 2‐Amino Septanosyl Glycoconjugates Using Septanosyl Fluoride Donors
  作者：Jaideep Saha、Mark W. Peczuh

  DOI：10.1002/chem.201003721

  日期：2011.6.20

  2‐Amino septanosyl fluorides were prepared from D‐glucose, D‐galactose, and D‐mannose. Other routes to the septanosyl glyconjugates, especially with regard to alternate donor types, were systematically investigated. Since routes to the individual donor types were being explored, factors that exert a controlling influence on the acid‐mediated cyclization of 1,6‐hydroxy‐aldehydes were determined. The newly

  已经开发了一种通用策略，可以对天然氨基糖苷的复杂，环状扩展类似物进行立体控制合成。该方法的核心是在容易的和选择性的糖基化反应中利用Septanosyl氟化物作为糖基供体。事实证明，Septanosyl氟化物是糖基化反应的最佳选择，因为它们的可及性和糖苷配基的范围很广。此外，在糖基化中观察到高度的立体选择性，仅产生1,2-反式-糖苷。由D-葡萄糖，D-半乳糖和D制备2-氨基庚烷氟甘露糖。系统地研究了生成Septanosyl糖缀合物的其他途径，尤其是关于其他供体类型的途径。由于正在探索通往各个供体类型的途径，因此确定了对酸介导的1,6-羟基醛类环化有控制作用的因素。新制备的2-氨基庚烷糖基糖缀合物说明了反应的范围以及如何将其用于制备糖基化天然产物的其他环扩类似物。