(+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate | 146383-91-7

• 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 (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate
• CAS: 146383-91-7
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: CGTMSOWETZVNKO-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以85%的产率得到Methyl (2R,3S)-3-(benzyloxy)-4-formyl-2-methoxybutanoate
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017
• 作为产物：
  描述：

  甲醇 、 (-)-(2R,3R)-3-Benzyloxy-4-hydroxy-2-methoxybutanoic acid 1,4-lactone 在 potassium carbonate 作用下， 反应 0.42h， 生成 (+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017