2-acetamido-2-deoxy-1,3,6-tri-O-pivaloyl-4-O-trifluoromethanesulfonyl-β-D-glucopyranose | 1258839-41-6

• 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-1,3,6-tri-O-pivaloyl-4-O-trifluoromethanesulfonyl-β-D-glucopyranose
• CAS: 1258839-41-6
• 化学式: C₂₄H₃₈F₃NO₁₁S
• 分子量: 605.627
• InChiKey: VPSIMDJFYJIQJN-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  160.6
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-1,3,6-tri-O-pivaloyl-4-O-trifluoromethanesulfonyl-β-D-glucopyranose 、 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以777 mg的产率得到4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-1,3,6-tri-O-pivaloyl-4-thio-β-D-galactopyranose
  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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2-acetamido-2-deoxy-1,3,6-di-O-pivaloyl-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-acetamido-2-deoxy-1,3,6-tri-O-pivaloyl-4-O-trifluoromethanesulfonyl-β-D-glucopyranose
  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