tert-butyl N-[(3S,4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]carbamate | 157823-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl N-[(3S,4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]carbamate
• CAS: 157823-88-6
• 化学式: C₁₆H₃₁NO₅Si
• 分子量: 345.511
• InChiKey: NPXWJKLWHRQMHD-NWDGAFQWSA-N

物化性质

• 沸点：
  428.3±38.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3S,4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]carbamate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Diastereoselective reactions of grignard reagents with chiral amino lactols derived firom L-aspartic acid

  摘要：

  Nucleophilic additions to chiral amino lactols obtained from L-aspartic acid containing a chiral alpha-silyloxymethyl function by simple Grignard reagents exhibited high stereoselectivity to provide the corresponding optically active amino alcohols containing three contiguous stereogenic centers. The mechanistic origin of the asymmetric induction is rationalized based on chelation controlled models.

  DOI：

  10.1016/s0957-4166(00)86164-9
• 作为产物：
  描述：

  BOC-L-天冬氨酸二甲酯 在 咪唑 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 lithium diisopropyl amide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 tert-butyl N-[(3S,4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]carbamate
  参考文献：
  名称：

  Diastereoselective reactions of grignard reagents with chiral amino lactols derived firom L-aspartic acid

  摘要：

  Nucleophilic additions to chiral amino lactols obtained from L-aspartic acid containing a chiral alpha-silyloxymethyl function by simple Grignard reagents exhibited high stereoselectivity to provide the corresponding optically active amino alcohols containing three contiguous stereogenic centers. The mechanistic origin of the asymmetric induction is rationalized based on chelation controlled models.

  DOI：

  10.1016/s0957-4166(00)86164-9

文献信息

• Diastereoselective reactions of grignard reagents with chiral amino lactols derived firom L-aspartic acid
  作者：Hidemi Yoda、Yoshiaki Nakagami、Kinihiko Takabe

  DOI：10.1016/s0957-4166(00)86164-9

  日期：1994.1

  Nucleophilic additions to chiral amino lactols obtained from L-aspartic acid containing a chiral alpha-silyloxymethyl function by simple Grignard reagents exhibited high stereoselectivity to provide the corresponding optically active amino alcohols containing three contiguous stereogenic centers. The mechanistic origin of the asymmetric induction is rationalized based on chelation controlled models.