tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-2-methylpropan-2-yl]carbamate | 869736-88-9

• 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: tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-2-methylpropan-2-yl]carbamate
• CAS: 869736-88-9
• 化学式: C₂₅H₃₇NO₄Si
• 分子量: 443.659
• InChiKey: SFVUWBZAVXDNLK-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-2-methylpropan-2-yl]carbamate 在 草酰氯 、 三氟化硼乙醚 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal
  参考文献：
  名称：

  Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

  摘要：

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.037
• 作为产物：
  描述：

  (1,3-二羟基-2-甲基-2-丙基)(2-甲基-2-丙基)氨基甲酸 在 sodium hydroxide 、 immobilized Pseudomonas sp. lipase 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 反应 3.0h， 生成 tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-2-methylpropan-2-yl]carbamate
  参考文献：
  名称：

  Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

  摘要：

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.037

文献信息

• Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one
  作者：Takashi Tsuji、Yukiko Iio、Toshiyasu Takemoto、Takahide Nishi

  DOI：10.1016/j.tetasy.2005.07.037

  日期：2005.10

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.