phenyl N-o-nitrobenzyl-2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-1-thio-α-D-glucopyranoside | 1352653-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl N-o-nitrobenzyl-2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-1-thio-α-D-glucopyranoside
• 英文别名: (3aR,4R,6R,7S,7aR)-7-hydroxy-3-[(2-nitrophenyl)methyl]-6-(phenylmethoxymethyl)-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1352653-33-8
• 化学式: C₂₇H₂₆N₂O₇S
• 分子量: 522.579
• InChiKey: KOLCXIFFXMCREX-ZFXZZAOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  phenyl N-o-nitrobenzyl-2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以55%的产率得到phenyl N-o-nitrobenzyl-2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Substituent effects in endocyclic cleavage–recyclization anomerization reaction of pyranosides

  摘要：

  Pyranosides with 2,3-trans carbamate or 2,3-trans carbonate groups are anomerized under mild acidic conditions via endocyclic cleavage reaction. In order to understand the nature of the anomerization reaction via the endocyclic cleavage recyclization process, the substituent effects at various positions were investigated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.059

文献信息

• Substituent effects in endocyclic cleavage–recyclization anomerization reaction of pyranosides
  作者：Shino Manabe、Kazuyuki Ishii、Hiroko Satoh、Yukishige Ito

  DOI：10.1016/j.tet.2011.09.059

  日期：2011.12

  Pyranosides with 2,3-trans carbamate or 2,3-trans carbonate groups are anomerized under mild acidic conditions via endocyclic cleavage reaction. In order to understand the nature of the anomerization reaction via the endocyclic cleavage recyclization process, the substituent effects at various positions were investigated. (C) 2011 Elsevier Ltd. All rights reserved.