4-pentenyl 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-β-D-glucopyranoside | 142269-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-pentenyl 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-β-D-glucopyranoside
• CAS: 142269-96-3
• 化学式: C₃₁H₄₁NO₉S
• 分子量: 603.734
• InChiKey: OIRWEPLXXVAOKV-FZFMXQKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129.62
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-pentenyl 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-β-D-glucopyranoside 在 iodonium dicollidine perchlorate 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-α-D-glucopyranose 、 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-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
• 作为产物：
  描述：

  4-pentenyl 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-4,6-O-(isopropylidene)-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 6.5h， 生成 4-pentenyl 2-allyloxycarbonylamino-3-O-benzyl-2-deoxy-6-O-(2,4,6-trimethylphenylsulfonyl)-β-D-glucopyranoside
  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