[(S)-[(1R,2R,6R,9R)-6-methyl-7-oxo-9-phenyl-4-sulfanylidene-3,5,10-trioxa-8-azatricyclo[6.3.0.02,6]undecan-1-yl]-phenylmethyl] acetate | 208706-90-5

• 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: [(S)-[(1R,2R,6R,9R)-6-methyl-7-oxo-9-phenyl-4-sulfanylidene-3,5,10-trioxa-8-azatricyclo[6.3.0.02,6]undecan-1-yl]-phenylmethyl] acetate
• CAS: 208706-90-5
• 化学式: C₂₃H₂₁NO₆S
• 分子量: 439.489
• InChiKey: BBEJWXKTPMYQHO-WOEVYDRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(S)-[(1R,2R,6R,9R)-6-methyl-7-oxo-9-phenyl-4-sulfanylidene-3,5,10-trioxa-8-azatricyclo[6.3.0.02,6]undecan-1-yl]-phenylmethyl] acetate 在 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 为溶剂， 生成 (3R,4S,5S)-4-Hydroxy-5-hydroxymethyl-5-((S)-hydroxy-phenyl-methyl)-3-methyl-pyrrolidin-2-one
  参考文献：
  名称：

  Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

  摘要：

  In the presence of BF3 . OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrol[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R, 7aR, 1'R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R, 7aR, 1'S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.

  DOI：

  10.3987/com-98-8123
• 作为产物：
  描述：

  (R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-3-phenyl-1H-pyrrolo[1,2-c]oxazole 在 四氧化锇 、 N-甲基吲哚酮 、 三氟化硼乙醚 作用下， 生成 [(S)-[(1R,2R,6R,9R)-6-methyl-7-oxo-9-phenyl-4-sulfanylidene-3,5,10-trioxa-8-azatricyclo[6.3.0.02,6]undecan-1-yl]-phenylmethyl] acetate
  参考文献：
  名称：

  Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

  摘要：

  In the presence of BF3 . OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrol[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R, 7aR, 1'R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R, 7aR, 1'S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.

  DOI：

  10.3987/com-98-8123