(S)-2-(2'-furyl)-2-(tert-butyldimethylsilyloxy)-acetonitrile | 139765-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (S)-2-(2'-furyl)-2-(tert-butyldimethylsilyloxy)-acetonitrile
• 英文别名: (S)-2-(2'-furyl)-2-O-(tert-butyldimethylsilyl)acetonitrile；(S)-(tert-butyldimethylsilanyloxy)furan-2-ylacetonitrile；(S)-2-(tert-butyldimethylsilyloxy)-2-(furan-2-yl)acetonitrile；(I+/-S)-I+/--[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-furanacetonitrile；(2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-(furan-2-yl)acetonitrile
• CAS: 139765-20-1
• 化学式: C₁₂H₁₉NO₂Si
• 分子量: 237.374
• InChiKey: RBGQWMAREHZQSU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.16
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(2'-furyl)-2-(tert-butyldimethylsilyloxy)-acetonitrile 在 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-furan-2-yl-1-methyl-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids and their application in the synthesis of an α-hydroxylated β-hexapeptide

  摘要：

  A chemoenzymatic, and stereoselective synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids from 2-furaldehyde is described as well as their application. without prior hydroxyl protection, in the solid-phase synthesis of a novel completely a-hydroxylated beta -hexapeptide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00193-8
• 作为产物：
  描述：

  糠醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 咪唑 、 R-oxynitrilase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-2-(2'-furyl)-2-(tert-butyldimethylsilyloxy)-acetonitrile
  参考文献：
  名称：

  Chemoenzymatic synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids and their application in the synthesis of an α-hydroxylated β-hexapeptide

  摘要：

  A chemoenzymatic, and stereoselective synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids from 2-furaldehyde is described as well as their application. without prior hydroxyl protection, in the solid-phase synthesis of a novel completely a-hydroxylated beta -hexapeptide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00193-8

文献信息

• Stereochemistry of intramolecular Diels–Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides
  作者：Reynier A. Tromp、Johannes Brussee、Arne van der Gen

  DOI：10.1039/b307275d

  日期：——

  describes the stereoselective outcome of the intramolecular Diels-Alder furan (IMDAF) reaction of substituted (2S,3S)-ethanolamides 9-13, which were synthesised from a furyl substituted cyanohydrin. The latter was obtained from 2-furaldehyde with high enantioselectivity by an oxynitrilase catalysed addition of hydrogen cyanide. The stereochemistry of the IMDAF products was shown to be dependent on the size

  本文描述了由呋喃基取代的氰醇合成的取代的（2S，3S）-乙醇酰胺9-13的分子内Diels-Alder呋喃（IMDAF）反应的立体选择性结果。后者是由2-呋喃甲醛以对映选择性高的方式通过氧硝化酶催化的氰化氢加成而获得的。结果表明，IMDAF产品的立体化学取决于乙醇酰胺取代基R的大小。较小的取代基（H，Me，CN）仅进行环外加成，而较大的取代基（Ph，Et）对内和外加此外，较大的苯基取代基具有较高的内-外比。
• Enantioselective Chemoenzymatic Synthesis of <i>trans</i>-Aziridines
  作者：Bas Ritzen、Matthijs C. M. van Oers、Floris L. van Delft、Floris P. J. T. Rutjes

  DOI：10.1021/jo901548t

  日期：2009.10.2

  straightforward, five-step procedure for the synthesis of enantiomerically pure 2,3-disubstituted trans-aziridines has been developed starting from commercially available aldehydes. Hydroxynitrile lyase-mediated cyanohydrin formation provided cyanohydrins in excellent enantioselectivities and good yields. Subsequent formation of diastereomerically pure anti-amino alcohols via a one-pot Grignard addition−reduction

  从可商购的醛开始，已经开发出用于合成对映体纯的2，3-二取代的反式氮丙啶的简单的五步程序。羟基腈裂解酶介导的氰醇的形成提供了优异的对映选择性和良好的产率的氰醇。随后通过一锅式格氏加成-还原序列，Cu II催化的重氮转移和三苯基膦介导的还原环化反应形成非对映体纯的抗氨基醇，从而以高收率和优异的非对映选择性提供了相应的反式-氮丙啶。
• Enantiomerically pure tetrahydroisoquinolines by enzyme catalysis and gold-catalyzed phenol synthesis
  作者：A. Stephen K. Hashmi、Filiz Ata、Patrick Haufe、Frank Rominger

  DOI：10.1016/j.tet.2008.12.058

  日期：2009.2

  Five different furfural derivatives were converted to chiral cyanohydrins by enzyme catalysis in good enantiomeric excess. After a sequence of silyl protection, nitrile reduction, tosylation and propargylation, substrates for the gold(I) catalyzed cycloisomerization of δ-alkynyl furans delivered good yields of enantiomerically pure dihydroxytetrahydroisoquinoline building blocks. Neither racemization

  通过良好的对映体过量，通过酶催化将五种不同的糠醛衍生物转化为手性氰醇。经过一系列的甲硅烷基保护，腈还原，甲苯磺酸酯化和炔丙基化反应后，金（I）催化的δ-炔基呋喃环异构化反应的底物获得了对映体纯的二羟基四氢异喹啉结构单元良好的收率。既没有消旋也没有消除喹啉。
• Synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids from a furyl substituted chiral cyanohydrin
  作者：Reynier A. Tromp、Michael van der Hoeven、Alessia Amore、Johannes Brussee、Mark Overhand、Gijs A. van der Marel、Arne van der Gen

  DOI：10.1016/s0957-4166(03)00218-0

  日期：2003.6

  A stereoselective chemoenzymatic synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids 6 is described. After the formation of cyanohydrin 2 from 2-furaldehyde in the presence of R-oxynitrilase and subsequent protection, 3 was transformed into fully protected ethanolamines 5. Ozonolysis provided the target compounds in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.