ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate | 294172-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate
• CAS: 294172-56-8
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: OJVHBZJOQSWRPU-YQQAZPJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate 在 lithium aluminium tetrahydride 、 正丁基锂 、 二异丁基氢化铝 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (Z)-1,6-anhydro-2-O-benzyl-3-{3',6'-[(benzyloxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099
• 作为产物：
  描述：

  氯甲酸苄酯 、 Ethyl 1,4,5-trideoxy-3,6-imino-4,5-O-isopropylidene-L-arabino-hexonate 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099