phenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-α-D-mannopyranoside | 945631-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5S,6R)-3,5-diacetyloxy-4-azido-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 945631-56-1
• 化学式: C₁₈H₂₁N₃O₇S
• 分子量: 423.447
• InChiKey: FAJCZRPFIDKVMI-MDMSPXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-α-D-mannopyranoside 在 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 phenyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-[4-(trifluoromethyl)benzylideneimino]-1-thio-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
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-D-mannopyranoside 、 苯硫酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到phenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-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