Boc-Cys(Bzl)-OEt | 110694-58-1

• 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: Boc-Cys(Bzl)-OEt
• 英文别名: ethyl (2R)-3-benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 110694-58-1
• 化学式: C₁₇H₂₅NO₄S
• 分子量: 339.456
• InChiKey: FTHUCLYLZXZHIV-AWEZNQCLSA-N

物化性质

• 沸点：
  474.5±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Cys(Bzl)-OEt 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 <(R)-3-(Benzylthio)-2-<(tert-butyloxycarbonyl)amino>propanoyl>hydrazine
  参考文献：
  名称：

  Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics

  摘要：

  Three series of heterocyclic dipeptidomimetics have been synthesized. The compounds were designed as amino acid-glycine mimetics containing 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole ring systems, useful as building blocks in the synthesis of modified peptides. The heterocyclic moieties were chosen according to their geometrical, electrostatical, and hydrogen bonding properties together with the synthetic accessibility. The syntheses started with Boc-protected L-amino acids (Ala, Gly, Asp, Phe, Ser, Arg, Cys, and Pro), and the reaction conditions were chosen to allow for the formation of products with high enantiopurity. The enantiomeric excess was determined by HPLC using chiral stationary phases.

  DOI：

  10.1021/jo00115a029
• 作为产物：
  描述：

  溴甲苯 、 N-Boc-L-cysteine ethyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 Boc-Cys(Bzl)-OEt
  参考文献：
  名称：

  Diastereoselective Alkylations of a Protected Cysteinesulfenate

  摘要：

  To further understand stereoselection in the alkylation of sulfenate anions, a protected cysteinesulfenate was generated in THF solution at low temperature. Introduction of a reactive alkylating agent brings about a cysteinyl sulfoxide in 51-75% yield, with diastereomeric ratios at the sulfinyl group ranging from 83:17 to 95:5. An internally complexed lithium counterion is proposed to account for the stereoselectivity.

  DOI：

  10.1021/jo901021r

文献信息

• Solventless Mechanosynthesis of N-Protected Amino Esters
  作者：Laure Konnert、Frédéric Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.1021/jo500463y

  日期：2014.5.2

  planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.

  N-或C-保护的氨基酸的机械化学衍生化是在无溶剂条件下在球磨机中进行的。用于制备甲振动球磨机ñ -保护的α-和β-氨基酯从相应的起始N-通过在二-的存在下，氨基甲酰反应未掩蔽的前体叔丁基酯（BOC 2 O），氯甲酸苄酯（Z-Cl）或9-芴基甲氧基羰基氯甲酸酯（Fmoc-Cl）。事实证明，行星式球磨机更适合通过一锅法从N保护的氨基酸合成氨基酯各种二碳酸二烷基酯或氯甲酸酯存在下的活化/酯化反应。点对点反应简单明了，从而缩短了反应时间，提高了收率，简化了后处理程序，从而使最终产品成为可能。
• Synthesis of amino acid esters by papain
  作者：D. Cantacuzène、F. Pascal、C. Guerreiro

  DOI：10.1016/s0040-4020(01)81493-9

  日期：1987.1
• Braun; Kuhl, Pharmazie, 1997, vol. 52, # 3, p. 203 - 206
  作者：Braun、Kuhl

  DOI：——

  日期：——
• Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics
  作者：Susanna Borg、Genevieve Estenne-Bouhtou、Kristina Luthman、Ingeborg Csoeregh、Willy Hesselink、Uli Hacksell

  DOI：10.1021/jo00115a029

  日期：1995.5

  Three series of heterocyclic dipeptidomimetics have been synthesized. The compounds were designed as amino acid-glycine mimetics containing 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole ring systems, useful as building blocks in the synthesis of modified peptides. The heterocyclic moieties were chosen according to their geometrical, electrostatical, and hydrogen bonding properties together with the synthetic accessibility. The syntheses started with Boc-protected L-amino acids (Ala, Gly, Asp, Phe, Ser, Arg, Cys, and Pro), and the reaction conditions were chosen to allow for the formation of products with high enantiopurity. The enantiomeric excess was determined by HPLC using chiral stationary phases.
• Diastereoselective Alkylations of a Protected Cysteinesulfenate
  作者：Adrian L. Schwan、Marcus J. Verdu、Suneel P. Singh、Jennifer S. O’Donnell、Amir Nasser Ahmadi

  DOI：10.1021/jo901021r

  日期：2009.9.4

  To further understand stereoselection in the alkylation of sulfenate anions, a protected cysteinesulfenate was generated in THF solution at low temperature. Introduction of a reactive alkylating agent brings about a cysteinyl sulfoxide in 51-75% yield, with diastereomeric ratios at the sulfinyl group ranging from 83:17 to 95:5. An internally complexed lithium counterion is proposed to account for the stereoselectivity.