Methyl-3-nitro-3-desoxy-α-D-mannopyranosid | 37073-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-3-nitro-3-desoxy-α-D-mannopyranosid
• 英文别名: Methyl-3-deoxy-3-nitro-α-D-mannopyranosid
• CAS: 37073-79-3
• 化学式: C₇H₁₃NO₇
• 分子量: 223.183
• InChiKey: PQPUXJMPHURQIH-UOYQFSTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.28
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  122.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methyl-3-nitro-3-desoxy-α-D-mannopyranosid 在 镍 硫酸 、 triflic azide 、 氢气 、 sodium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 41.0h， 生成 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-β-D-mannopyranoside
  参考文献：
  名称：

  Direct Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides:  Importance of the Nitrogen Protecting Group on Stereoselectivity

  摘要：

  The highly stereocontrolled synthesis of the 3-amino-3-deoxy-beta-mannopyranosides is achieved by means of thioglycoside donors protected with a 4,6-O-benzylidene or alkylidene acetal and a benzylidene imine group. Among the various nitrogen protecting groups investigated only the Schiff's base was found to give high beta-selectivity. N-Phthalimido and N-acetamido protected donors were found to be highly alpha-selective, whereas 3-azido-3-deoxy glycosyl donors gave intermediate selectivity. The reasons for the protecting group dependency are discussed in terms of the change in the O2-C2-C3-N3 torsional interaction on conversion of the covalent glycosyl triflates to the transient oxacarbenium ions.

  DOI：

  10.1021/jo070473p
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 sodium periodate 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 9.5h， 生成 Methyl-3-nitro-3-desoxy-α-D-mannopyranosid
  参考文献：
  名称：

  Direct Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides:  Importance of the Nitrogen Protecting Group on Stereoselectivity

  摘要：

  The highly stereocontrolled synthesis of the 3-amino-3-deoxy-beta-mannopyranosides is achieved by means of thioglycoside donors protected with a 4,6-O-benzylidene or alkylidene acetal and a benzylidene imine group. Among the various nitrogen protecting groups investigated only the Schiff's base was found to give high beta-selectivity. N-Phthalimido and N-acetamido protected donors were found to be highly alpha-selective, whereas 3-azido-3-deoxy glycosyl donors gave intermediate selectivity. The reasons for the protecting group dependency are discussed in terms of the change in the O2-C2-C3-N3 torsional interaction on conversion of the covalent glycosyl triflates to the transient oxacarbenium ions.

  DOI：

  10.1021/jo070473p