methyl 3-azido-3-deoxy-α-D-mannopyranoside | 945631-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-4-azido-2-(hydroxymethyl)-6-methoxyoxane-3,5-diol
• CAS: 945631-54-9
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: WUXIOHNNHKEPKP-UOYQFSTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-α-D-mannopyranoside 、 三苯基氯甲烷 以82%的产率得到
  参考文献：
  名称：

  TADANO, KIN-ICHI;HOTTA, YUKINORI;;MORITA, MASAHIRO;SUAMI, TETSUO;WINCHEST+, BULL. CHEM. SOC. JAP., 60,(1987) N 10, 3667-3671

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 镍 sodium periodate 、 triflic azide 、 氢气 、 sodium methylate 、 sodium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， -10.0~20.0 ℃ 、344.75 kPa 条件下， 反应 38.5h， 生成 methyl 3-azido-3-deoxy-α-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

文献信息

• Direct Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides:  Importance of the Nitrogen Protecting Group on Stereoselectivity
  作者：David Crich、Huadong Xu

  DOI：10.1021/jo070473p

  日期：2007.7.1

  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.
• TADANO, KIN-ICHI;HOTTA, YUKINORI;;MORITA, MASAHIRO;SUAMI, TETSUO;WINCHEST+, BULL. CHEM. SOC. JAP., 60,(1987) N 10, 3667-3671
  作者：TADANO, KIN-ICHI、HOTTA, YUKINORI、、MORITA, MASAHIRO、SUAMI, TETSUO、WINCHEST+

  DOI：——

  日期：——