(4R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-4-<(tert-butyldiphenylsilyl)oxy>-2-cyclohepten-1-one | 151936-86-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-4-<(tert-butyldiphenylsilyl)oxy>-2-cyclohepten-1-one
• 英文别名: (4R,6S)-6-[(tert-Butyldimethylsilyl)oxy]-4-[(tert-butyldiphenylsilyl)oxy]-2-cyclohepten-1-one；(4R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-4-[tert-butyl(diphenyl)silyl]oxycyclohept-2-en-1-one
• CAS: 151936-86-6
• 化学式: C₂₉H₄₂O₃Si₂
• 分子量: 494.822
• InChiKey: UBIZTIHIOXLAJL-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-4-<(tert-butyldiphenylsilyl)oxy>-2-cyclohepten-1-one 在 Wilkinson's catalyst 二甲基硫 、 氧气 、 臭氧 作用下， 以 乙醚 为溶剂， 反应 5.17h， 生成 (3R,6S)-Methyl 3-<(tert-butyldimethylsilyl)oxy>-5-<(tert-butyldiphenylsilyl)oxy>-7-oxoheptanoate
  参考文献：
  名称：

  Enantio- and diastereoselective transformations of cycloheptatriene to sugars and related products

  摘要：

  Both meso diastereomers of 6-[(tert-butyldimethylsilyl)oxy]-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.

  DOI：

  10.1021/jo00077a049
• 作为产物：
  描述：

  (1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol 在 咪唑 、 氢氧化钾 、 4 A molecular sieve 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (4R,6S)-6-<(tert-Butyldimethylsilyl)oxy>-4-<(tert-butyldiphenylsilyl)oxy>-2-cyclohepten-1-one
  参考文献：
  名称：

  Enantio- and diastereoselective transformations of cycloheptatriene to sugars and related products

  摘要：

  Both meso diastereomers of 6-[(tert-butyldimethylsilyl)oxy]-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.

  DOI：

  10.1021/jo00077a049

文献信息

• Enantio- and diastereoselective transformations of cycloheptatriene to sugars and related products
  作者：Carl R. Johnson、Adam Golebiowski、Darryl H. Steensma、Mark A. Scialdone

  DOI：10.1021/jo00077a049

  日期：1993.12

  Both meso diastereomers of 6-[(tert-butyldimethylsilyl)oxy]-2-cycloheptene-1,4-diol, prepared from cycloheptatriene, have been enzymatically asymmetrized by conversion to monoacetates using Pseudomonas cepacia lipase in isopropenyl acetate. A study of protecting group manipulations, diastereoselective oxidations, and regioselective ring openings utilizing these enantiopure monacetates which results in the synthesis of all possible methyl 2,4-dideoxyhexopyranosides is described.