(S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-thiocarboxy-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester | 682353-88-4

• 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: (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-thiocarboxy-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester
• 英文别名: (3S)-4-[[(2S)-3-methyl-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanethioic S-acid
• CAS: 682353-88-4
• 化学式: C₂₃H₃₉N₃O₇S
• 分子量: 501.645
• InChiKey: QNUFGVDOVWMJKO-ZOBUZTSGSA-N

物化性质

• 沸点：
  675.1±55.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  azidomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 、 (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-thiocarboxy-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester 在 2,6-二甲基吡啶 作用下， 以 氯仿 为溶剂， 以72%的产率得到(S)-1-((S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanylmethyl)-carbamoyl]-propionylamino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Novel S-Neoglycopeptides from Glycosylthiomethyl Derivatives

  摘要：

  Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate and glutamate thio acids gave the corresponding glycosylthiomethyl amides in excellent yields. Another type of neoglycopeptides was obtained via reaction of glycosylthiomethyl bromide with cysteine and homocysteine containing peptide derivatives, thus affording the corresponding S-(glycosylthiomethyl) peptides.

  DOI：

  10.1021/ol036186z
• 作为产物：
  描述：

  (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-carboxy-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester 在 硫化氢 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-thiocarboxy-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Novel S-Neoglycopeptides from Glycosylthiomethyl Derivatives

  摘要：

  Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate and glutamate thio acids gave the corresponding glycosylthiomethyl amides in excellent yields. Another type of neoglycopeptides was obtained via reaction of glycosylthiomethyl bromide with cysteine and homocysteine containing peptide derivatives, thus affording the corresponding S-(glycosylthiomethyl) peptides.

  DOI：

  10.1021/ol036186z