(2R,3R)-3-Chlorocarbonyl-2,3-dimethoxy-propionic acid methyl ester | 27957-95-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R)-3-Chlorocarbonyl-2,3-dimethoxy-propionic acid methyl ester
• CAS: 27957-95-5
• 化学式: C₇H₁₁ClO₅
• 分子量: 210.614
• InChiKey: YQIPWEZVVQBVCV-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Chlorocarbonyl-2,3-dimethoxy-propionic acid methyl ester 在 氨 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2R,3R)-4-amino-2,3-dimethoxy-4-oxobutanoate
  参考文献：
  名称：

  Totalsynthese des Antibioticums Anisomycin

  摘要：

  AbstractThe synthesis of the antibiotic anisomycin (1) is described. In the key step 3, 4‐dimethoxy‐thiopyrrolidone (16), prepared from diethyl L‐( + )‐tartarate (4) was converted to the thioiminoester 18, which upon treatment with trimethylphosphite yielded the benzylidene derivative 19. Cleavage of the ester group of 19 and hydrogenation of the decarboxylation product gave the two isomers 21 and 22. 22 was converted into desacetylanisomycin (3) and anisomycin (1).

  DOI：

  10.1002/hlca.19700530409
• 作为产物：
  描述：

  dextrorotatory α.α'-dimethoxy-succinic acid monomethyl ester 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-3-Chlorocarbonyl-2,3-dimethoxy-propionic acid methyl ester
  参考文献：
  名称：

  Totalsynthese des Antibioticums Anisomycin

  摘要：

  AbstractThe synthesis of the antibiotic anisomycin (1) is described. In the key step 3, 4‐dimethoxy‐thiopyrrolidone (16), prepared from diethyl L‐( + )‐tartarate (4) was converted to the thioiminoester 18, which upon treatment with trimethylphosphite yielded the benzylidene derivative 19. Cleavage of the ester group of 19 and hydrogenation of the decarboxylation product gave the two isomers 21 and 22. 22 was converted into desacetylanisomycin (3) and anisomycin (1).

  DOI：

  10.1002/hlca.19700530409