1-adamantanyl 3-amino-2-O-benzyl-3-deoxy-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-β-D-mannopyranoside | 945631-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-adamantanyl 3-amino-2-O-benzyl-3-deoxy-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-β-D-mannopyranoside
• 英文别名: (2S,4aR,6S,7S,8S,8aS)-6-(1-adamantyloxy)-8-amino-2-[(2-iodophenyl)methyl]-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2-carbonitrile
• CAS: 945631-77-6
• 化学式: C₃₂H₃₇IN₂O₅
• 分子量: 656.561
• InChiKey: UZKKMIUPFNJLTH-YHNINBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-adamantanyl 3-amino-2-O-benzyl-3-deoxy-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-β-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 xylene 为溶剂， 反应 2.0h， 以20%的产率得到N-[(2S,3S,4S,5S,6R)-2-(1-adamantyloxy)-5-hydroxy-6-methyl-3-phenylmethoxyoxan-4-yl]-2-(2-cyanophenyl)acetamide
  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：

  在 二苯基亚砜 、 三氟化硼乙醚 、 trifluoromethanesulfonic acid anhydride 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 26.25h， 生成 1-adamantanyl 3-amino-2-O-benzyl-3-deoxy-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-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