methyl 6-O-tert-butyldimethylsilyl-2,3,7-trideoxy-3,7-imino-4,5-O-isopropylidene-D-gluco-heptonate | 196406-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-tert-butyldimethylsilyl-2,3,7-trideoxy-3,7-imino-4,5-O-isopropylidene-D-gluco-heptonate
• 英文别名: methyl 2-[(3aR,4R,7S,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]acetate
• CAS: 196406-65-2
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: OGLKKQPVKWWIMV-AYRXBEOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-O-tert-butyldimethylsilyl-2,3,7-trideoxy-3,7-imino-4,5-O-isopropylidene-D-gluco-heptonate 在 盐酸 、 氘代甲醇 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 76.0h， 生成
  参考文献：
  名称：

  The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine

  摘要：

  1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4-8 in six steps and 23-32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27-29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-alpha,beta-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4-8 afforded the piperidine and indolizidine imino sugars 9-12 and 14-15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00794-1
• 作为产物：
  描述：

  1-(N-tert-butoxycarbonyl)amino-1-deoxy-3,4-O-isopropylidene-D-glucitol 在 sodium periodate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 methyl 6-O-tert-butyldimethylsilyl-2,3,7-trideoxy-3,7-imino-4,5-O-isopropylidene-D-gluco-heptonate
  参考文献：
  名称：

  The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine

  摘要：

  1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4-8 in six steps and 23-32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27-29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-alpha,beta-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4-8 afforded the piperidine and indolizidine imino sugars 9-12 and 14-15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00794-1