3,4-di-O-acetyl-2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-D-glucopyranose | 142269-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4-di-O-acetyl-2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-D-glucopyranose
• CAS: 142269-88-3
• 化学式: C₁₄H₁₉NO₈
• 分子量: 329.307
• InChiKey: VGXVCGJKYUIQBY-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-N-Allyloxycarbonyl-2-amino-1,6-anhydro-2-deoxy-β-D-glucopyranose 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以12%的产率得到3,4-di-O-acetyl-2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Selective protections on 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-β-d-glucopyranose

  摘要：

  Regioselective monoacetylation of 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-beta-D-glucopyranose (1) gave a mixture of 3-O-acetyl and 4-O-acetyl derivatives, the structures of which were established by two-dimensional, phase-sensitive NOESY and confirmed by chemical proofs. The benzylation of 1, on the other hand, led to 2-allyloxycarbonylamino-1,6-anhydro-3,4-di- (5) or 2-allyloxycarbonylamino-1,6-anhydro-2 -N-benzyl-3,4-di-O-benzyl-2-deoxy-beta-D-glucopyranose (10). The regioselective cleavage of 5 with titanium tetrachloride gave the expected 3-O-benzyl derivative, the structure of which was ascertained by chemical proofs; the same reaction performed on 10 led to the opening of the anhydro ring to afford 3-benzyl-[3,4-di-O-benzyl-1,2-dideoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazolidone.

  DOI：

  10.1016/s0008-6215(00)90550-0