2,6-dibromo-2,6-dideoxy-3,4-O-isopropylidene-D-glucitol | 938065-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dibromo-2,6-dideoxy-3,4-O-isopropylidene-D-glucitol
• 英文别名: (2S)-2-bromo-2-[(4S,5R)-5-[(1S)-2-bromo-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 938065-91-9
• 化学式: C₉H₁₆Br₂O₄
• 分子量: 348.032
• InChiKey: ZLYCCEZILUPBEH-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-2,6-dideoxy-3,4-O-isopropylidene-D-glucitol 在 吡啶 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 6-amino-2-bromo-1-O-t-butyldimethylsilyl-2,6-dideoxy-3,4-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)

  摘要：

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.110
• 作为产物：
  描述：

  2,6-Dibromo-2,6-dideoxy-D-glucono-1,4-lactone 在 sodium tetrahydroborate 、 H⁽¹⁺⁾ resin 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 0.08h， 生成 2,6-dibromo-2,6-dideoxy-3,4-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)

  摘要：

  1-Deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ) were synthesized through a concise and practicable pathway. A strategy of using carbohydrate derivatives bearing two leaving groups in the preparation of azasugars by di-N-alkylation of amines was developed. The strategy involved the selective partial protection of dibromo alditols. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.110