methyl 4-azido-2,6-di-O-benzyl-4-deoxy-α-D-galactopyranoside | 688341-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-azido-2,6-di-O-benzyl-4-deoxy-α-D-galactopyranoside
• 英文别名: (2S,3R,4S,5R,6S)-5-azido-2-methoxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-ol
• CAS: 688341-33-5
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: LAVLCLGRVIOFBK-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-2,6-di-O-benzyl-4-deoxy-α-D-galactopyranoside 在 四氮唑 、 NCCH₂CH₂OP(N(i-Pr)2)OCH₂CH₂NHFmoc 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以90%的产率得到methyl 4-deoxy-2,6-di-O-benzyl-3-keto-α-D-galactopyranoside
  参考文献：
  名称：

  A New Reaction for the Direct Conversion of 4-Azido-4-deoxy-d-galactoside into a 4-Deoxy-d-erythro-hexos-3-ulose

  摘要：

  A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite A intermediate and a tetrazole-catalyzed elimination reaction of the resultant phosphorimidate. Tetrazole appears to be playing a unique role by acting as a bifunctional catalyst to facilitate the elimination reaction.

  DOI：

  10.1021/ol0499046
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-azido-2,6-di-O-benzyl-4-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  A New Reaction for the Direct Conversion of 4-Azido-4-deoxy-d-galactoside into a 4-Deoxy-d-erythro-hexos-3-ulose

  摘要：

  A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite A intermediate and a tetrazole-catalyzed elimination reaction of the resultant phosphorimidate. Tetrazole appears to be playing a unique role by acting as a bifunctional catalyst to facilitate the elimination reaction.

  DOI：

  10.1021/ol0499046

文献信息

• A New Reaction for the Direct Conversion of 4-Azido-4-deoxy-<scp>d</scp>-galactoside into a 4-Deoxy-<scp>d</scp>-<i>e</i><i>rythro</i>-hexos-3-ulose
  作者：Jie Xue、Jian Wu、Zhongwu Guo

  DOI：10.1021/ol0499046

  日期：2004.4.1

  A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite A intermediate and a tetrazole-catalyzed elimination reaction of the resultant phosphorimidate. Tetrazole appears to be playing a unique role by acting as a bifunctional catalyst to facilitate the elimination reaction.