benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate | 86122-64-7

• 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
• 英文名称: benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate
• 英文别名: dibenzyl (2S,3S)-3-methylaziridine-1,2-dicarboxylate
• CAS: 86122-64-7
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: KCSOTXCFIPSYOB-OJIYZUOWSA-N

物化性质

• 沸点：
  454.1±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate 在 三氟化硼乙醚 、 硫化氢 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,3S)-2-Benzyloxycarbonylamino-3-mercapto-butyric acid benzyl ester
  参考文献：
  名称：

  2-氮丙啶羧酸的研究。X. 光学活性胱氨酸和threo-3,3'-二甲基胱氨酸的简单立体定向合成

  摘要：

  (2S)-Z-Azy-OBzl、(2S,3S)-Z-3-MeAzy-OBzl 及其对映异构体与 H2S 的反应通过立体特异性开环得到光学活性半胱氨酸和 thero-3-甲基半胱氨酸衍生物氮丙啶反应，随后的氧化和解封闭程序以良好的产率得到标题化合物。

  DOI：

  10.1246/bcsj.56.1565
• 作为产物：
  描述：

  benzyl (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylate 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate
  参考文献：
  名称：

  One-step synthesis of optically active benzyl N-trityl-L-aziridine-2-carboxylic esters

  摘要：

  Benzyl N-trityl-L-serine or threonine esters give upon treatment with sulphuryl chloride the corresponding benzyl (2S)-1-trityl-2-aziridine carboxylate or (2S, 3S)-1-trityl-3-methyl-2-aziridinecarboxylate esters in excellent yields.

  DOI：

  10.1016/s0040-4039(00)79586-4

文献信息

• Studies on 2-Aziridinecarboxylic Acid. IX. Convenient Synthesis of Optically Active<i>S</i>-Alkylcysteine,<i>threo</i>-<i>S</i>-Alkyl-β-methylcysteine, and Lanthionine Derivatives<i>via</i>the Ring-opening Reaction of Aziridine by Several Thiols
  作者：Kiichiro Nakajima、Hitomi Oda、Kenji Okawa

  DOI：10.1246/bcsj.56.520

  日期：1983.2

  and benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate, and their enantiomers were treated with several thiols, and the corresponding S-alkylcysteine, threo-S-alkyl-β-methylcysteine, and lanthionine derivatives were prepared via the ring-opening reaction of aziridine in the presence of a catalytic amount of boron trifluoride etherate in good yields.

  已经研究了光学活性 S-烷基半胱氨酸、苏-S-烷基-β-甲基半胱氨酸和羊毛硫氨酸衍生物的方便合成。1-苄氧羰基-(2S)-2-氮丙啶羧酸苄酯和(2S,3S)-1-苄氧羰基-3-甲基-2-氮丙啶羧酸苄酯及其对映体用几种硫醇处理，相应的S-烷基半胱氨酸、苏- S-烷基-β-甲基半胱氨酸和羊毛硫氨酸衍生物通过氮丙啶在催化量的三氟化硼醚合物存在下的开环反应以良好的产率制备。
• Novel O-glycosyl amino acid mimetics as building blocks for O-glycopeptides act as inhibitors of galactosidases
  作者：Lars Kröger、Dirk Henkensmeier、Andreas Schäfer、Joachim Thiem

  DOI：10.1016/j.bmcl.2003.10.011

  日期：2004.1

  6-anhydro-D-glycero-L-gluco-heptitol-1-yl]-L-serine 3 and-L-threonine 4 were synthesized, employing regio- and stereoselective aziridine ring opening methodology. They proved to be stable in the presence of glycosidases and showed competitive inhibition of alpha-galactosidase from Aspergillus niger.

  作为新型糖苷酶抑制剂的潜在先导结构，新型O-糖基氨基酸模拟物3'-O- [2,6-脱水-D-甘油-L-葡萄糖-庚醇-1-基] -L-丝氨酸3通过使用区域和立体选择性氮丙啶开环方法合成了α-L和苏氨酸4。它们被证明在糖苷酶存在下是稳定的，并显示出来自黑曲霉的α-半乳糖苷酶的竞争性抑制作用。
• Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics
  作者：Andreas Schäfer、Dirk Henkensmeier、Lars Kröger、Joachim Thiem

  DOI：10.1016/j.tetasy.2009.02.038

  日期：2009.5

  Glycosyl amino acid mimetics of the typical GalNAc-(1 -> O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics. (C) 2009 Elsevier Ltd. All rights reserved.