2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine | 77611-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine
• 英文别名: [(2R,3R,4S,5R,6R)-2-amino-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 77611-19-9
• 化学式: C₂₉H₃₃NO₆
• 分子量: 491.584
• InChiKey: DDCVEIWUAFGSNJ-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 为溶剂， 生成 1-acetamido-2,3,4,6-tetraacetyl-1-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of N-glycosides. Formation of glucosylamine by reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with acetonitrile in the presence of trifluoromethanesulfonic anhydride

  摘要：

  DOI：

  10.1021/jo00328a045
• 作为产物：
  描述：

  (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以46%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Ritter-like reactions of 1,2-anhydropyranose derivatives

  摘要：

  DOI：

  10.1021/jo00011a050

文献信息

• Neighboring-Group Participation by C-2 Ether Functions in Glycosylations Directed by Nitrile Solvents
  作者：Chin-Sheng Chao、Ching-Yu Lin、Shaheen Mulani、Wei-Cheng Hung、Kwok-kong Tony Mong

  DOI：10.1002/chem.201100732

  日期：2011.10.17

  Ether‐protecting functions at C‐2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C‐2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2‐cis glycosyl

  当在腈溶剂混合物中进行反应时，已发现在C-2羟基处的醚保护功能在糖基化中起参与作用。参与机制基于C-2醚功能的氧原子的孤电子对和腈分子以顺式排列时的分子内相互作用。形成一个1,2-顺式糖基恶唑啉鎓中间体。这种参与，再加上糖基供体的异头作用，赋予糖基化较高的1,2-反式选择性。该概念的进一步应用导致了α-（1→5）-阿拉伯低聚物的高效制备。
• Synthesis and Biological Evaluation of a Backbone-Modified Phytoalexin Elicitor
  作者：C. M. Timmers、J. J. Turner、C. M. Ward、G. A. van der Marel、M. L. C. E. Kouwijzer、P. D. J. Grootenhuis、J. H. van Boom

  DOI：10.1002/chem.19970030614

  日期：1997.6

  AbstractTwo suitably protected building blocks (11 and 33) for the preparation of amide‐linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt‐catalyzed condensation and two‐step conversion of the C6‐OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin‐elicitor activity.
• GORDON, DANA M.;DANISHEFSKY, SAMUEL J., J. ORG. CHEM., 56,(1991) N1, C. 3713-3715
  作者：GORDON, DANA M.、DANISHEFSKY, SAMUEL J.

  DOI：——

  日期：——