Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-bromomethylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester | 682353-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-bromomethylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(bromomethylsulfanyl)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 682353-97-5
• 化学式: C₁₆H₂₁BrCl₃NO₉S
• 分子量: 589.673
• InChiKey: LONXGLNHNIZGAK-KSTCHIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-bromomethylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 在 三乙胺 、 锌 作用下， 反应 3.0h， 生成 (S)-2-[(S)-2-tert-Butoxycarbonylamino-4-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-ylsulfanylmethylsulfanyl)-butyrylamino]-3-methyl-pentanoic acid methyl 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：

  、 二溴甲烷 在 potassium carbonate 作用下， 以49%的产率得到Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-bromomethylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl 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