(2'S,3'S)-6-amino-2-bromo-1-O-t-butyldimethylsilyl-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-iditol | 938065-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,3'S)-6-amino-2-bromo-1-O-t-butyldimethylsilyl-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-iditol
• 英文别名: (1S)-2-amino-1-[(2R,3S,5S,6S)-3-[(1S)-1-bromo-2-[tert-butyl(dimethyl)silyl]oxyethyl]-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]ethanol
• CAS: 938065-84-0
• 化学式: C₁₈H₃₈BrNO₆Si
• 分子量: 472.492
• InChiKey: MNEXAORYBHAFJX-ZUHXYLFWSA-N

物化性质

• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'S,3'S)-6-amino-2-bromo-1-O-t-butyldimethylsilyl-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-iditol 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.5h， 生成 去氧野艽霉素盐酸盐
  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：

  叔丁基二甲基氯硅烷 、 2,6-dibromo-2,6-dideoxy-L-iditol 、 2,2,3,3-四甲氧基丁烷 在 三氟化硼乙醚 、 吡啶 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以28%的产率得到(2'S,3'S)-6-amino-2-bromo-1-O-t-butyldimethylsilyl-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-iditol
  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

文献信息

• Facile syntheses of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ)
  作者：Xuezheng Song、Rawle I. Hollingsworth

  DOI：10.1016/j.tetlet.2007.01.110

  日期：2007.4

  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.