1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-β-D-galactopyranose | 1085337-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-β-D-galactopyranose
• CAS: 1085337-52-5
• 化学式: C₁₄H₂₉NO₆Si
• 分子量: 335.473
• InChiKey: PJHYONFZOVTCFK-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  108.25
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-β-D-galactopyranose 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以48%的产率得到1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-β-D-galactopyranose
  参考文献：
  名称：

  Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-O-Nucleophiles. Stereoselective Preparation of α- and β-O-Glycosyl Serine Conjugates

  摘要：

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.

  DOI：

  10.1021/ja804589j
• 作为产物：
  描述：

  1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-D-galactopyranose 在 甲醇 、 potassium carbonate 作用下， 反应 1.5h， 生成 1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-α-D-galactopyranose 、 1-O-(tert-butyldimethylsilyl)-2-acetamido-2-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-O-Nucleophiles. Stereoselective Preparation of α- and β-O-Glycosyl Serine Conjugates

  摘要：

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.

  DOI：

  10.1021/ja804589j