ethyl (2R)-3-but-3-enylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1263182-21-3

• 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: ethyl (2R)-3-but-3-enylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1263182-21-3
• 化学式: C₁₄H₂₅NO₄S
• 分子量: 303.423
• InChiKey: PDAACLOXFTUZDL-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1-硫代-b-D-葡萄糖四乙酸酯 、 ethyl (2R)-3-but-3-enylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 安息香双甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以93%的产率得到ethyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylbutylsulfanyl]propanoate
  参考文献：
  名称：

  Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling

  摘要：

  We report on the photoinduced addition of glycosyl thiols to alkenyl glycines (thiol-ene coupling) to give S-glycosyl amino acids in high yields (53-90%). One of the amino acids thus prepared was used in the construction of a tripeptide via solution phase chemistry. Moreover, a one-pot two-step approach to an S-glycopeptide was developed using glutathione (GSH) as model starting material. This approach involved GSH S-alkenylation followed by photoinduced hydrothiolation by a glycosyl thiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.097
• 作为产物：
  描述：

  4-溴-1-丁烯 、 N-Boc-L-cysteine ethyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以87%的产率得到ethyl (2R)-3-but-3-enylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling

  摘要：

  We report on the photoinduced addition of glycosyl thiols to alkenyl glycines (thiol-ene coupling) to give S-glycosyl amino acids in high yields (53-90%). One of the amino acids thus prepared was used in the construction of a tripeptide via solution phase chemistry. Moreover, a one-pot two-step approach to an S-glycopeptide was developed using glutathione (GSH) as model starting material. This approach involved GSH S-alkenylation followed by photoinduced hydrothiolation by a glycosyl thiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.097