p-methylphenyl 2-N-acetyl-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-glucopyranoside | 1379678-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-N-acetyl-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-glucopyranoside
• CAS: 1379678-14-4
• 化学式: C₂₀H₂₃NO₈S
• 分子量: 437.471
• InChiKey: GWNJPNGUSXDTTN-FVVUREQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  p-tolyl 4,6-di-O-acetyl-2-deoxy-2-N-acetyl-1-thio-β-D-glucopyranosid[2,3-d]-1,3-oxazolidin-2-one 、 甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 四丁基三氟甲磺酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到methyl (N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-diacetyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

  摘要：

  用低温电化学氧化从硫代糖苷生成带有2,3-噁唑啉醇保护基的糖基三氟甲磺酸酯。糖基三氟甲磺酸酯与醇在低温下反应，选择性地形成相应的糖苷β-选择性产物。然而，在高温反应条件下，在无碱存在的情况下观察到α-选择性。原位生成的三氟甲磺酸促进β-产物向α-产物的异构化。

  DOI：

  10.3762/bjoc.8.52

文献信息

• Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol
  作者：Qi Qin、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1016/j.carres.2014.07.004

  日期：2015.2

  Stereo-controllable glycosylation reactions of 2,3-oxazolidinone protected glucosamine thioglycoside donor with different phenol acceptors based on preactivation protocol, are described. It was found that BF3.Et2O worked as alpha-directing additive, while TTBP acted as beta-directing additive. Simply by altering additives, either alpha-aryl glycosides or beta-aryl glycosides were achieved in a stereoselective manner. The additives were also applied to the stereoselective glycosylation reactions of 2,3-oxazolidinone protected galactosamine donor with phenol substrates. (C) 2014 Elsevier Ltd. All rights reserved.