cis-N-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidin-2-one | 123076-56-2

• 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: cis-N-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidin-2-one
• 英文别名: cis-N-(tert-butoxycarbonyl)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}pyrrolidin-2-one；tert-butyl (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxopyrrolidine-1-carboxylate
• CAS: 123076-56-2；123163-94-0；130192-99-3
• 化学式: C₂₂H₄₅NO₅Si₂
• 分子量: 459.774
• InChiKey: BYYYLDDXIGOIIZ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-N-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidin-2-one 在 铂 氢氧化钾 、 四丁基氟化铵 、 氧气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.5h， 生成
  参考文献：
  名称：

  Electrophilic olefin heterocyclization in organic synthesis. Stereoselective synthesis of 4,5-disubstituted .gamma.-lactams by iodine-induced lactam formation of .gamma.,.delta.-unsaturated thioimidates

  摘要：

  DOI：

  10.1021/jo00281a022
• 作为产物：
  描述：

  cis-N-benzyl-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidin-2-one 在 sodium 、 sodium hydride 作用下， 以 氨 为溶剂， 反应 10.0h， 生成 cis-N-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-5-<<(tert-butyldimethylsilyl)oxy>methyl>pyrrolidin-2-one
  参考文献：
  名称：

  Electrophilic olefin heterocyclization in organic synthesis. Stereoselective synthesis of 4,5-disubstituted .gamma.-lactams by iodine-induced lactam formation of .gamma.,.delta.-unsaturated thioimidates

  摘要：

  DOI：

  10.1021/jo00281a022

文献信息

• Influences of Catalyst Configuration and Catalyst Loading on Selectivities in Reactions of Diazoacetamides. Barrier to Equilibrium between Diastereomeric Conformations
  作者：Michael P. Doyle、Wenhao Hu、Andrew G. H. Wee、Zhongyi Wang、Sammy C. Duncan

  DOI：10.1021/ol027157b

  日期：2003.2.1

  [reaction: see text] Stereoelectronic factors present a barrier to equilibrium between diastereomeric conformations resulting in differences in selectivity as a function of catalyst configuration. The bis(trimethylsilyl)-methyl protective group is inert to insertion but directs carbon-hydrogen insertion with enhanced enantiocontrol.

  [反应：见正文]立体电子因素为非对映异构构象之间的平衡提供了障碍，导致选择性差异随催化剂构型而变化。双（三甲基甲硅烷基）-甲基保护基对于插入是惰性的，但是在增强对映体控制的情况下指导碳-氢插入。
• Tkahata, Hiroki; Tajima, Mayumi; Banba, Yasunori, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 9, p. 2550 - 2552
  作者：Tkahata, Hiroki、Tajima, Mayumi、Banba, Yasunori、Momose, Takefumi

  DOI：——

  日期：——
• 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
  作者：Hiroki Takahata、Yasunori Banba、Mayumi Tajima、Takefumi Momose

  DOI：10.1021/jo00001a045

  日期：1991.1

  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.
• 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：——