methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-β-D-glucopyranoside | 639504-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4S,5R,6R)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]acetonitrile
• CAS: 639504-87-3
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: NDZNJHZIANQKEC-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-β-D-glucopyranoside 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 208.0h， 生成 1,5-bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranos-6-yl)-1H-tetrazole
  参考文献：
  名称：

  Synthesis of Nitrogen Heterocycles from Methyl α‐ and β‐d‐Glucopyranosides

  摘要：

  Eight nitrogen heterocycles, mono and disubstituted tetrazoles and oxadiazoles, were synthesized from methyl D-glucopyranoside anomers. The monosubstituted tetrazoles resulted from the reaction of 6-cyanoglucopyranoside derivatives with sodium azide. By alkylation of the monosubstituted tetrazoles, the 1,5 and 2,5 disubstituted tetrazoles were obtained. The monosubstituted tetrazoles were reacted with acetic anhydride to give the oxadiazoles.

  DOI：

  10.1081/car-120025329
• 作为产物：
  描述：

  氰化钾 、 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 以74%的产率得到methyl 2,3,4-tri-O-benzyl-6-cyano-6-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Nitrogen Heterocycles from Methyl α‐ and β‐d‐Glucopyranosides

  摘要：

  Eight nitrogen heterocycles, mono and disubstituted tetrazoles and oxadiazoles, were synthesized from methyl D-glucopyranoside anomers. The monosubstituted tetrazoles resulted from the reaction of 6-cyanoglucopyranoside derivatives with sodium azide. By alkylation of the monosubstituted tetrazoles, the 1,5 and 2,5 disubstituted tetrazoles were obtained. The monosubstituted tetrazoles were reacted with acetic anhydride to give the oxadiazoles.

  DOI：

  10.1081/car-120025329

文献信息

• Synthesis of Nitrogen Heterocycles from Methyl α‐ and β‐<scp>d</scp>‐Glucopyranosides
  作者：Maria Teresa Capanema Pedrosa、Rosemeire Brondi Alves、Maria Auxiliadora Fontes Prado、José Dias de Souza Filho、Ricardo José Alves、Norma Beatriz D'Accorso

  DOI：10.1081/car-120025329

  日期：2003.1.10

  Eight nitrogen heterocycles, mono and disubstituted tetrazoles and oxadiazoles, were synthesized from methyl D-glucopyranoside anomers. The monosubstituted tetrazoles resulted from the reaction of 6-cyanoglucopyranoside derivatives with sodium azide. By alkylation of the monosubstituted tetrazoles, the 1,5 and 2,5 disubstituted tetrazoles were obtained. The monosubstituted tetrazoles were reacted with acetic anhydride to give the oxadiazoles.