Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester | 688341-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester
• CAS: 688341-52-8
• 化学式: C₂₄H₂₇F₃O₉S
• 分子量: 548.534
• InChiKey: GIZRPTPHVOMOJF-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester 在 四氮唑 、 sodium hydroxide 、 sodium azide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 ((2S,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl)-phosphoramidic acid dimethyl ester
  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：

  甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Acetic acid (2S,3R,4R,5R,6R)-3-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester
  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