6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxynojirimycin | 938065-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxynojirimycin
• 英文别名: (3aR,4R,7S,7aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 938065-90-8
• 化学式: C₁₅H₃₁NO₄Si
• 分子量: 317.501
• InChiKey: RGDSVMLBTUHDLX-YVECIDJPSA-N

物化性质

• 沸点：
  398.2±42.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxynojirimycin 在 盐酸 作用下， 以 甲醇 为溶剂， 以96%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：

  L-古洛糖酸-gamma-内酯 在 对甲苯磺酸 吡啶 、 ammonium hydroxide 、 sodium acetate 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 14.08h， 生成 6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-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.