(R)-2-氧代四氢呋喃-3-基氨基甲酸叔丁酯 | 67198-86-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (R)-2-氧代四氢呋喃-3-基氨基甲酸叔丁酯
• 中文别名: N-Boc-D-高丝氨酸内酯；2-氧代-四氢呋喃-3-氨基甲酸-(R)-叔丁酯
• 英文名称: (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone
• 英文别名: (R)-tert-butyl 2-oxotetrahydrofuran-3-ylcarbamate；(2-oxotetrahydro-furan-3(R)-yl)-carbamic acid tert-butyl ester；(R)-N-(tert-butoxycarbonyl)homoserine lactone；N-t-butyloxycarbonyl D-homoserine lactone；Boc-D-Homoserine lactone；tert-butyl N-[(3R)-2-oxooxolan-3-yl]carbamate
• CAS: 67198-86-1
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: IMWMFJMYEKHYKG-ZCFIWIBFSA-N

物化性质

• 熔点：
  115-118 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  363.7±31.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (R)-2-氧代四氢呋喃-3-基氨基甲酸叔丁酯 在 sodium hydroxide 、 dimethyl azodicarboxylate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 生成 -propoxy>phenyl>glyoxylic acid
  参考文献：
  名称：

  D-高丝氨酸的手性合成及其在诺卡霉素A合成中的应用

  摘要：

  DOI：

  10.1016/s0040-4039(01)91502-3
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 chromium(VI) oxide 、 palladium on activated charcoal 过氧乙酸 、 氢气 、 potassium acetate 、 potassium hydrogencarbonate 、 高碘酸 、 三氟乙酸 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 12.5h， 生成 (R)-2-氧代四氢呋喃-3-基氨基甲酸叔丁酯
  参考文献：
  名称：

  Silylcupration of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine:  A Stereoselective Approach to the Synthesis of γ-Silylated Saturated and Unsaturated α-Amino Acids

  摘要：

  Enantioselective synthesis of gamma-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final-compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, beta,gamma-unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.

  DOI：

  10.1021/jo991272r

文献信息

• Ring Opening of a Trisubstituted Aziridine With Amines: Regio- and Stereoselective Formation of Substituted 1,2-Diamines
  作者：Brandon T. Kelley、Madeleine M. Joullié

  DOI：10.1021/ol101584z

  日期：2010.10.1

  substituted 1,2-diamines via nucleophilic ring opening of a trisubstituted ethynyl aziridine was performed with complete regio- and stereoselective control. Various amines with different levels of nucleophilicity were employed and gave similar results. The ring opening reaction is not limited to ethynyl aziridines, as other alkyl trisubstituted aziridines gave the same results. This method allows for

  通过三取代的乙炔基氮丙啶的亲核开环形成取代的1，2-二胺是在完全的区域和立体选择性控制下进行的。使用了具有不同亲核性水平的各种胺，并得出了相似的结果。开环反应不限于乙炔基氮丙啶，因为其他烷基三取代的氮丙啶也得到相同的结果。该方法允许形成独特的邻位二胺，同时在温和条件下以立体选择性的方式提供完全取代的碳中心。
• A New Stereocontrolled Approach to a Key Intermediate in the Synthesis of (2S,3R)-Capreomycidine
  作者：Miroslava Martinková、Jozef Gonda、Martina Džoganová

  DOI：10.1135/cccc20061199

  日期：——

  A new stereocontrolled approach to the synthesis of advanced intermediate in the synthesis of nonproteinogenic amino acid (2S,3R)-capreomycidine via the novel domino reaction has been developed.

  一种新的立体控制方法已经被开发出来，用于合成非蛋白氨基酸（2S,3R）-卡普雷霉胺的高级中间体。这种方法通过新颖的多米诺反应实现。
• Sulfonyl Containing Compounds as Cysteine Protease Inhibitors
  申请人：Mossman Craig J.

  公开号：US20080287446A1

  公开（公告）日：2008-11-20

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及抑制半胱氨酸蛋白酶的化合物，特别是猫蛋白酶B、K、L、F和S，因此在治疗由这些蛋白酶介导的疾病方面非常有用。本发明涉及包含这些化合物的制药组合物和制备它们的方法。
• SULFONYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
  申请人：Mossman Craig

  公开号：US20110281879A1

  公开（公告）日：2011-11-17

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及抑制半胱氨酸蛋白酶的化合物，特别是抑制B、K、L、F和S型蛋白酶，因此在治疗由这些蛋白酶介导的疾病中有用。本发明涉及包含这些化合物的制药组合物和其制备方法。
• Sulfonyl containing compounds as cysteine protease inhibitors
  申请人：ViroBay, Inc.

  公开号：US07893093B2

  公开（公告）日：2011-02-22

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及一类半胱氨酸蛋白酶抑制剂化合物，特别是针对B、K、L、F和S等猫蛋白酶，因此可用于治疗由这些蛋白酶介导的疾病。本发明涉及包含这些化合物的制药组合物和制备它们的过程。