[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-hydroxyoxan-2-yl]methyl acetate | 824985-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 824985-67-3
• 化学式: C₁₂H₁₉NO₈
• 分子量: 305.285
• InChiKey: CPMQHYGMLDFCGW-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-hydroxyoxan-2-yl]methyl acetate 在 甲醇 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 magnesium 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 2-乙酰氨基-1-氨基-1,2-二脱氧-beta-D-吡喃葡萄糖
  参考文献：
  名称：

  Rapid Formation of N-Glycopeptides via Cu(II)-Promoted Glycosylative Ligation

  摘要：

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.

  DOI：

  10.1021/ol302961s
• 作为产物：
  描述：

  D-glucosamine hydrochloride 、 乙酸酐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-hydroxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Rapid Formation of N-Glycopeptides via Cu(II)-Promoted Glycosylative Ligation

  摘要：

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.

  DOI：

  10.1021/ol302961s