(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester | 1174725-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester
• CAS: 1174725-65-5
• 化学式: C₂₄H₃₂N₂O₁₁
• 分子量: 524.525
• InChiKey: KZUOHMXBDZRQFC-KZXFCMPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  178.78
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester 、 Fmoc-D-苯丙氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以68%的产率得到N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069
• 作为产物：
  描述：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine benzyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

  摘要：

  This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.069