O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinol | 518986-06-6

• 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: O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinol
• 英文别名: Boc-N(MeOH)Ser(TBDMS)(TBDMS)-ol；tert-butyl N-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropan-2-yl]-N-(hydroxymethyl)carbamate
• CAS: 518986-06-6
• 化学式: C₁₅H₃₃NO₅Si
• 分子量: 335.516
• InChiKey: WKJFWVHSNSYPRY-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以70%的产率得到(R)-(+)-N-(叔丁氧基羰基)-O-(叔丁基二甲基甲硅烷基)丝氨酸醇
  参考文献：
  名称：

  Efficient Synthesis of a Configurationally Stable l-Serinal Derivative

  摘要：

  An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.

  DOI：

  10.1021/jo026653a
• 作为产物：
  描述：

  (2S)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyloxy)propionic acid 在 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.75h， 生成 O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinol
  参考文献：
  名称：

  Efficient Synthesis of a Configurationally Stable l-Serinal Derivative

  摘要：

  An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.

  DOI：

  10.1021/jo026653a

文献信息

• Efficient Synthesis of a Configurationally Stable <scp>l</scp>-Serinal Derivative
  作者：Dongwon Yoo、Joon Seok Oh、Dong-Whal Lee、Young Gyu Kim

  DOI：10.1021/jo026653a

  日期：2003.4.1

  An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.