(4S,5R)-4-(hydroxymethyl)-4,5-dimethyloxazolidin-2-one | 677344-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-4-(hydroxymethyl)-4,5-dimethyloxazolidin-2-one
• 英文别名: (4S,5R)-4-(hydroxymethyl)-4,5-dimethyl-1,3-oxazolidin-2-one
• CAS: 677344-64-8
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: OSCAZKLPLHTJSK-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(hydroxymethyl)-4,5-dimethyloxazolidin-2-one 在 盐酸 、 jones reagent 作用下， 以 水 、 丙酮 为溶剂， 反应 53.0h， 生成 (2R,3R)-2-铵基-3-羟基-2-甲基丁酸酯
  参考文献：
  名称：

  α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: application in the synthesis of all stereoisomers of α-methylthreonine

  摘要：

  The asymmetric synthesis of all stereoisomers of alpha-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different beta-substituted alpha-methylserines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.001
• 作为产物：
  描述：

  (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (4S,5R)-4-(hydroxymethyl)-4,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: application in the synthesis of all stereoisomers of α-methylthreonine

  摘要：

  The asymmetric synthesis of all stereoisomers of alpha-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different beta-substituted alpha-methylserines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.001

文献信息

• α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: application in the synthesis of all stereoisomers of α-methylthreonine
  作者：Alberto Avenoza、Jesús H. Busto、Francisco Corzana、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/j.tetasy.2003.12.001

  日期：2004.2

  The asymmetric synthesis of all stereoisomers of alpha-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different beta-substituted alpha-methylserines. (C) 2003 Elsevier Ltd. All rights reserved.