(2S)-3-叠氮基-2-羟基-2-甲基-丙酸甲酯 | 549504-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S)-3-叠氮基-2-羟基-2-甲基-丙酸甲酯
• 英文名称: (2S)-3-Azido-2-hydroxy-2-methyl-propanoic acid methyl ester
• 英文别名: methyl (2S)-3-azido-2-hydroxy-2-methylpropanoate
• CAS: 549504-45-2
• 化学式: C₅H₉N₃O₃
• 分子量: 159.145
• InChiKey: IFZQXKZFIXWPKR-YFKPBYRVSA-N

物化性质

• 溶解度：
  可溶于丙酮、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基2,3-二羟基-2-甲基丙酸酯 在 氯化亚砜 、 sodium azide 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 (2S)-3-叠氮基-2-羟基-2-甲基-丙酸甲酯
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

  摘要：

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha -methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary alpha -amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-alpha -methylserinal building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00159-8

文献信息

• Enzyme-Catalyzed Nucleophilic Ring Opening of Epoxides for the Preparation of Enantiopure Tertiary Alcohols
  作者：Maja Majerić Elenkov、H. Wolfgang Hoeffken、Lixia Tang、Bernhard Hauer、Dick B. Janssen

  DOI：10.1002/adsc.200700146

  日期：2007.10.8

  dehalogenase from Agrobacterium radiobacter AD1 (HheC) catalyzes nucleophilic ring opening of epoxides with cyanide and azide. In the case of 2,2-disubstituted epoxides, this reaction proceeds with excellent enantioselectivity (E values up to>200), which gives, by kinetic resolution, access to various enantiopure epoxides and β-substituted tertiary alcohols (ee up to 99 %). Since the enzyme has a broad

  根癌土壤杆菌AD1（HheC）的卤代醇脱卤酶催化氰化物和叠氮化物对环氧化物的亲核开环。在2,2-二取代的环氧化物的情况下，该反应以优异的对映选择性（E值最高> 200）进行，通过动力学拆分，可以得到各种对映纯的环氧化物和β-取代的叔醇（ee高达99％ ）。由于该酶具有广泛的底物范围，并且由于这些叔醇难以用其他方式制备，因此HheC是生产β-氰基和β-叠氮基叔醇的有吸引力的生物催化剂。
• Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals
  作者：Alberto Avenoza、Carlos Cativiela、Francisco Corzana、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(01)00159-8

  日期：2001.4

  This report describes the synthesis of enantiomerically pure (S)- and (R)-alpha -methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary alpha -amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-alpha -methylserinal building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective Synthesis of α-Methyl-<scp>d</scp>-cysteine and Lanthionine Building Blocks via α-Methyl-<scp>d</scp>-serine-β-lactone
  作者：Nicole D. Smith、Murray Goodman

  DOI：10.1021/ol034025p

  日期：2003.4.1

  [GRAPHICS]We report here the enantioselective synthesis of Boc-alpha-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regloselective ring opening of key intermediate Boc-alpha-methyl-D-serine-beta-lactone.