p-tolyl N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-O-diacetyl-2-deoxy-1-thio-β-D-galactopyranoside | 1242060-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-O-diacetyl-2-deoxy-1-thio-β-D-galactopyranoside
• 英文别名: p-tolyl 2-acetamino-4,6-di-O-acetyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-galactopyranoside
• CAS: 1242060-76-9
• 化学式: C₂₀H₂₃NO₈S
• 分子量: 437.471
• InChiKey: GWNJPNGUSXDTTN-FQBWVUSXSA-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

• 作为反应物：
  描述：

  p-tolyl N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-O-diacetyl-2-deoxy-1-thio-β-D-galactopyranoside 在 4-甲基苯硫氯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 phenyl N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol

  摘要：

  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.

  DOI：

  10.1016/j.carres.2014.07.004
• 作为产物：
  描述：

  p-tolyl 2-amino-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-galactopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以88%的产率得到p-tolyl N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-O-diacetyl-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol

  摘要：

  根据预激活方案，可通过添加剂控制噁唑烷酮保护的氨基糖硫代糖苷给体对糖基化的立体选择性。通过改变添加剂可获得δ-或δ-选择性。2,4,6-三叔丁基嘧啶（TTBP）是最好的δ-定向添加剂，而噻吩则是最好的δ-定向添加剂。双功能添加剂，如四丁基碘化铵（TBAI），根据添加量的不同，可提供δ-或δ-选择性。添加 TBAI 或噻吩后，一些未添加任何添加剂的糖基化反应的δ-选择性大大提高。

  DOI：

  10.1055/s-0030-1258557

文献信息

• A highly α-selective glycosylation for the convenient synthesis of repeating α-(1→4)-linked N-acetyl-galactosamine units
  作者：Lin Yang、Xin-Shan Ye

  DOI：10.1016/j.carres.2010.05.031

  日期：2010.8

  The repeating GalpNAc-alpha-(1 -> 4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1 -> 4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.