(2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol | 799559-97-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol
• 英文别名: tert-butyl N-[(2S,3S)-6-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-1-phenylsulfanylhexan-3-yl]carbamate
• CAS: 799559-97-0
• 化学式: C₂₃H₄₁NO₄SSi
• 分子量: 455.734
• InChiKey: QEWPBDCDHYVWQM-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,E)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-1-phenylsulfonyl-1-hexene
  参考文献：
  名称：

  Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones

  摘要：

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.

  DOI：

  10.1021/jo0268456
• 作为产物：
  描述：

  (E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol 在 palladium on activated charcoal titanium(IV) isopropylate 、 叔丁基过氧化氢 、 Ti(N3)2(OiPr)2 、 偶氮二甲酸二异丙酯 、 氢气 、 D-(-)-酒石酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 苯 为溶剂， 反应 8.5h， 生成 (2S,3S)-3-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsiloxy)-1-phenylthio-2-hexanol
  参考文献：
  名称：

  Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones

  摘要：

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.

  DOI：

  10.1021/jo0268456

文献信息

• Enantiodivergent, Catalytic Asymmetric Synthesis of γ-Amino Vinyl Sulfones
  作者：Anna Picó、Albert Moyano、Miquel A. Pericàs

  DOI：10.1021/jo0268456

  日期：2003.6.1

  A set of diversely substituted N-Boc-gamma-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of alpha-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given gamma-amino vinyl sulfone can be obtained with equal ease.