p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside | 1258839-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside
• CAS: 1258839-49-4
• 化学式: C₂₆H₃₆ClNO₈S
• 分子量: 558.093
• InChiKey: SRDPAGJHCUHQSN-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside 在 吡啶 、 triflic azide 、 copper(II) sulfate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 生成 p-chlorophenyl 2-azido-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Forssman antigen derivative for use in a conjugate vaccine

  摘要：

  The total chemical synthesis of a Forssman antigen analog is described. The pentasaccharide contains a functionalized tether which should facilitate future conjugation with immunogenic proteins. We found that the total synthesis can be efficiently achieved by following a convergent 2+3 strategy, and using N-Troc protected GalNAc thioglycoside as a donor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.015
• 作为产物：
  描述：

  2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranosyl chloride 、 4-氯苯硫酚 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以2.96 g的产率得到p-chlorophenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-pivaloyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  An efficient conversion of N-acetyl-d-glucosamine to N-acetyl-d-galactosamine and derivatives

  摘要：

  2-Acetamido-2-deoxy-D-galactose (D-GalNAc) is an important monosaccharide widely distributed in nature. However, unlike its 4-epimer, the 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-GalNAc is very expensive to obtain from commercial sources. Herein we report an efficient transformation that allows for the conversion of D-GlcNAc to a D-GalNAc derivative 7 in three steps and in 58.4-75% overall yields. The process was carried out on a greater than 20-g scale without the need of chromatography. The versatility of compound 7 was demonstrated by the synthesis of several useful monosaccharides and thiodisaccharides containing a D-GalNAc residue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.008