3,4,6-Triazido-3,4,6-tridesoxy-1,2-O-isopropyliden-α-D-glucopyranose | 69434-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-Triazido-3,4,6-tridesoxy-1,2-O-isopropyliden-α-D-glucopyranose
• 英文别名: 3,4,6-triazido-O¹,O²-isopropylidene-α-D-3,4,6-trideoxy-glucopyranose；(3aR)-6t,7c-diazido-5c-azidomethyl-2,2-dimethyl-(3ar,7ac)-tetrahydro-[1,3]dioxolo[4,5-b]pyran
• CAS: 69434-59-9
• 化学式: C₉H₁₃N₉O₃
• 分子量: 295.261
• InChiKey: WIDWJWMATWVBGN-JAJWTYFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  173.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,4,6-Triazido-3,4,6-tridesoxy-1,2-O-isopropyliden-α-D-glucopyranose 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 反应 3.25h， 生成 3,4,6-Triacetamido-3,4,6-tridesoxy-D-glucose
  参考文献：
  名称：

  Meyer zu Reckendorf, Wolfgang; Spohr, Ulrike, Liebigs Annalen der Chemie, 1981, # 11, p. 1982 - 1993

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-Diazido-3,6-didesoxy-1,2-O-isopropyliden-α-D-glucopyranose 在 sodium benzoate 、 sodium azide 、 sodium methylate 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 3,4,6-Triazido-3,4,6-tridesoxy-1,2-O-isopropyliden-α-D-glucopyranose
  参考文献：
  名称：

  Meyer zu Reckendorf, Wolfgang; Spohr, Ulrike, Liebigs Annalen der Chemie, 1981, # 11, p. 1982 - 1993

  摘要：

  DOI：

文献信息

• Synthetic Approach to 2,3,5-Triamino-2,3,5-trideoxy-D-arabonic Acid Derivatives from 3,4,6-Triazido-3,4,6-trideoxy-1,2-<i>O</i>-isopropylidene-α-D-glucopyranose
  作者：Mitsuhiro Kinoshita、Shinpei Aburaki、Yasuyuki Kawada、Takumi Yamasaki、Yoshiharu Suzuki、Yoichi Niimura

  DOI：10.1246/bcsj.51.3261

  日期：1978.11

  3,6-Diazido-3,6-dideoxy-1,2-O-isopropylidene-α-d-glucofuranose was converted into the corresponding derivative of α-d-glucopyranose, which was transformed into 3,4,6-triazido-3,4,6-trideoxy-1,2-O-isopropylidene-α-d-glucopyranose (7) through the sequence of reactions involving displacement of sulfonate ester function with benzoate, followed by debenzoylation, sulfonylation, and nucleophilic substitution. Hydrogenolysis of 7 afforded the corresponding triamino derivative 8. The tri-N-benzyloxycarbonyl derivative of 8 was O-deisopropylidenated and oxidized with periodate to afford the piperidinose derivative 11, deformylation of which yielded 2,3,5-tris(benzyloxycarbonylamino)-2,3,5-trideoxy-d-arabinopyranose (13). “Pfitzner-Moffatt” oxidation of 11 failed to give the corresponding lactam 15. Condensation of the 6-N-benzyloxycarbonyl derivative of 8 (18) with cyanogen bromide afforded the cyclic guanidine derivative (20) hydrobromide. The triazido derivative 7 was converted into 3,4,6-tris(benzyloxycarbonylamino)-3,4,6-trideoxy-d-glucitol (23), which was then oxidized successively with periodate and chromium trioxide-acetic acid-pyridine to give 2,3,5-tris(benzyloxycarbonylamino)-2,3,5-trideoxy-d-arabono-1,4-lactone (25); this was further transformed into 2,3,5-trianimo-2,3,5-trideoxy-d-arabono-1,5-lactam (16).

  阿拉伯糖-1,4-内酯（26）。