(2'S,3'S)-6-O-t-butyldimethylsilyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-deoxynojirimycin

• 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-O-t-butyldimethylsilyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-deoxynojirimycin
• 英文别名: (2S,3S,4aR,5R,8S,8aR)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,3-dimethoxy-2,3-dimethyl-4a,5,6,7,8,8a-hexahydro-[1,4]dioxino[2,3-c]pyridin-8-ol
• 化学式: C₁₈H₃₇NO₆Si
• 分子量: 391.58
• InChiKey: FMXMCDZZTKIDCH-UJARPBSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.4
• 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-O-t-butyldimethylsilyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-deoxynojirimycin 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到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：

  (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 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以74%的产率得到(2'S,3'S)-6-O-t-butyldimethylsilyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-deoxynojirimycin
  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.