Boc-Cys((O)-E-carbomethoxyethenyl)-OEt

• 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((O)-E-carbomethoxyethenyl)-OEt
• 英文别名: ethyl (2R)-3-[(E)-3-methoxy-3-oxoprop-1-enyl]sulfinyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₁₄H₂₃NO₇S
• 分子量: 349.405
• InChiKey: KCAGONGPUTZTPB-JTVMUNAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-Boc-Cys[(E)-2-carbomethoxyethenyl]-OEt	1139270-16-8	C14H23NO6S	333.406

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Boc-Cys((O)-4-MeBn)-OEt	1186227-27-9	C18H27NO5S	369.482
  ——	Boc-Cys((O)-4-CNBn)-OEt	1186227-31-5	C18H24N2O5S	380.465
  ——	Boc-Cys((O)-4-BrBn)-OEt	1186227-28-0	C17H24BrNO5S	434.351
  ——	Boc-Cys((O)-2-BrBn)-OEt	1186227-33-7	C17H24BrNO5S	434.351
  ——	Boc-Cys((O)-2-CHOBn)-OEt	1186227-34-8	C18H25NO6S	383.466
  ——	Boc-Cys((O)-2-CNBn)-OEt	1186227-32-6	C18H24N2O5S	380.465
  ——	Boc-Cys((O)-3-MeOBn)-OEt	1186227-29-1	C18H27NO6S	385.481
  ——	Boc-Cys((O)-3-NO2Bn)-OEt	1186227-30-4	C17H24N2O7S	400.453

反应信息

• 作为反应物：
  描述：

  Boc-Cys((O)-E-carbomethoxyethenyl)-OEt 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 Boc-Cys((O)-Bn)-OEt
  参考文献：
  名称：

  β-Sulfinyl acrylate esters as a convenient source of alkane- and arenesulfenate anions

  摘要：

  Methyl acrylate esters bearing alkane- and arenesulfinyl units on the 2-carbon liberate sulfenate anions upon nucleophilic attack. The sulfenates are readily captured through sulfur alkylation. When a sulfenate derived from R-cysteine is generated, diastereoselective benzylation is observed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01521-1
• 作为产物：
  描述：

  (R)-Boc-Cys[(E)-2-carbomethoxyethenyl]-OEt 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以4.28 g的产率得到Boc-Cys((O)-E-carbomethoxyethenyl)-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

• β-Sulfinyl acrylate esters as a convenient source of alkane- and arenesulfenate anions
  作者：Jennifer S. O'Donnell、Adrian L. Schwan

  DOI：10.1016/s0040-4039(03)01521-1

  日期：2003.8

  Methyl acrylate esters bearing alkane- and arenesulfinyl units on the 2-carbon liberate sulfenate anions upon nucleophilic attack. The sulfenates are readily captured through sulfur alkylation. When a sulfenate derived from R-cysteine is generated, diastereoselective benzylation is observed. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.