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 | 1187830-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 1187830-20-1
• 化学式: C₅₇H₅₅NO₈
• 分子量: 882.066
• InChiKey: FZPLJRRHYCNEND-MYXAWFEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  66
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  1
• 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,4R,5R,6R)-6-hydroxy-1-oxo-3,4,5,7-tetrakis(phenylmethoxy)heptan-2-yl]carbamate 在 二乙胺基三氟化硫 作用下， 生成 9H-fluoren-9-ylmethyl N-benzyl-N-[(3S,4S,5R,6R,7R)-2-fluoro-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)oxepan-3-yl]carbamate
  参考文献：
  名称：

  缺少C2保护基的Septanosylfluoro捐助者的糖基化

  摘要：

  由受保护的吡喃糖酶制备的Septanosyl氟化物用作糖基化反应的供体。通过将乙烯基格利雅（Grignard）添加到吡喃糖中，然后进行臭氧分解，然后进行DAST介导的氟化反应来合成氟化物。然后在亲核试剂存在下活化提供了产物糖苷。使用具有游离C 2羟基的供体观察到糖基化的高α-立体选择性。提出了一个羟基参与指导立体化学结果的模型。

  DOI：

  10.1016/j.tetlet.2012.08.039
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl benzyl((3R,4S,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90%的产率得到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
  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

• Glycosylations with a septanosyl fluoride donor lacking a C2 protecting group
  作者：Jaideep Saha、Mark W. Peczuh

  DOI：10.1016/j.tetlet.2012.08.039

  日期：2012.10

  Septanosyl fluorides, prepared from protected pyranoses, were used as donors in glycosylation reactions. The fluorides were synthesized by the addition of vinyl Grignard to the pyranoses followed by ozonolysis and then DAST-mediated fluorination. Activation in the presence of nucleophiles then provided the product glycosides. High α-stereoselectivity was observed for glycosylations using a donor that

  由受保护的吡喃糖酶制备的Septanosyl氟化物用作糖基化反应的供体。通过将乙烯基格利雅（Grignard）添加到吡喃糖中，然后进行臭氧分解，然后进行DAST介导的氟化反应来合成氟化物。然后在亲核试剂存在下活化提供了产物糖苷。使用具有游离C 2羟基的供体观察到糖基化的高α-立体选择性。提出了一个羟基参与指导立体化学结果的模型。
• Access to Ring-Expanded Analogues of 2-Amino Sugars
  作者：Jaideep Saha、Mark W. Peczuh

  DOI：10.1021/ol9018387

  日期：2009.10.1

  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.