(2R,3R)-2-<(1,1-dimethylethyl)dimethylsilyl>oxy-3-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine | 123287-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R)-2-<(1,1-dimethylethyl)dimethylsilyl>oxy-3-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine
• 英文别名: (2R,3R)-1-(tert-Butoxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-<(tert-butyldimethylsilyl)oxy>-pyrrolidine；tert-butyl (2R,3R)-3-(tert-butyldimethylsiloxy)-2-[(tertbutyldimethylsiloxy)methyl]pyrrolidine-1-carboxylate；(2R,3R)-1-(tert-Butoxycarbonyl)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-3-[(tert-butyldimethylsilyl)oxy]-pyrrolidine；tert-butyl (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidine-1-carboxylate
• CAS: 123287-87-6
• 化学式: C₂₂H₄₇NO₄Si₂
• 分子量: 445.79
• InChiKey: SPPXONJQIUVECY-QZTJIDSGSA-N

物化性质

• 沸点：
  427.7±30.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-<(1,1-dimethylethyl)dimethylsilyl>oxy-3-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以59%的产率得到(4R,5R)-N-(tert-Butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>-methyl>pyrrolidin-2-one
  参考文献：
  名称：

  Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds

  摘要：

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.

  DOI：

  10.1021/jo00001a045
• 作为产物：
  描述：

  (4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one 在 咪唑 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (2R,3R)-2-<(1,1-dimethylethyl)dimethylsilyl>oxy-3-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine
  参考文献：
  名称：

  Ewing, William R.; Joullie, Madeleine M., Heterocycles, 1988, vol. 27, # 12, p. 2843 - 2850

  摘要：

  DOI：

文献信息

• Asymmetric Syntheses of All Stereoisomers of 3-Hydroxyproline; A Constituent of Several Bioactive Compounds
  作者：Srivari Chandrasekhar、Togapur Kumar

  DOI：10.1055/s-0032-1316734

  日期：——

  3-hydroxyproline, and its derivatives have been achieved enantioselectively by employing Sharpless asymmetric epoxidation and reductive cyclization as the key steps. Synthesis of an unusual β-hydroxy-α-amino acid, 3-hydroxyproline, and its derivatives have been achieved enantioselectively by employing Sharpless asymmetric epoxidation and reductive cyclization as the key steps.

  摘要 通过使用Sharpless不对称环氧化和还原环化作为关键步骤，对映体选择性合成了一种不寻常的β-羟基-α-氨基酸，3-羟基脯氨酸及其衍生物。 通过使用Sharpless不对称环氧化和还原环化作为关键步骤，对映体选择性合成了一种不寻常的β-羟基-α-氨基酸，3-羟基脯氨酸及其衍生物。
• TAKAHATA, HIROKI;TAKAMATSU, TAMOTSU;YAMAZAKI, TAKAO, J. ORG. CHEM., 54,(1989) N0, C. 4812-4822
  作者：TAKAHATA, HIROKI、TAKAMATSU, TAMOTSU、YAMAZAKI, TAKAO

  DOI：——

  日期：——
• TAKAHATA, HIROKI;TAJIMA, MAYUMI;BANBA, YASUNORI;MOMOSE, TAKEFUMI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2550-2552
  作者：TAKAHATA, HIROKI、TAJIMA, MAYUMI、BANBA, YASUNORI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——
• TAKAHATA, HIROKI;BANBA, YASUNORI;TAJIMA, MAYUMI;MOMOSE, TAKEFUMI, J. ORG. CHEM., 56,(1991) N, C. 240-245
  作者：TAKAHATA, HIROKI、BANBA, YASUNORI、TAJIMA, MAYUMI、MOMOSE, TAKEFUMI

  DOI：——

  日期：——