2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranose
• 英文别名: pivaloyl(-3)[pivaloyl(-6)]b-GlcNAc；[(2R,3S,4R,5R,6R)-5-acetamido-4-(2,2-dimethylpropanoyloxy)-3,6-dihydroxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₁₈H₃₁NO₈
• 分子量: 389.446
• InChiKey: NKZSQPBPKRAMIH-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-GlcNAc 、 三甲基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以79.4%的产率得到2-acetamido-2-deoxy-1,3,6-di-O-pivaloyl-β-D-glucopyranoside
  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

文献信息

• An efficient conversion of N-acetyl-d-glucosamine to N-acetyl-d-galactosamine and derivatives
  作者：Jianhao Feng、Chang-Chun Ling

  DOI：10.1016/j.carres.2010.09.008

  日期：2010.11

  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.