1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide | 270062-18-5

• 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: 1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide
• 英文别名: (2R,3S,4R,5R)-5-hydroxy-N,2,3,4,6-pentakis(phenylmethoxy)hexanamide
• CAS: 270062-18-5
• 化学式: C₄₁H₄₃NO₇
• 分子量: 661.795
• InChiKey: SOHVNKIQZNYMFW-OPGJLUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide 在 二异丁基氢化铝 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 2,3,4,6-tetra-O-benzyl-L-idopyranose
  参考文献：
  名称：

  A Novel and Practical Synthesis of l-Hexoses from d-Glycono-1,5-lactones

  摘要：

  A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, delta-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. None of the N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into the L-sugars.

  DOI：

  10.1021/ja992808t
• 作为产物：
  描述：

  5-内酯 、 O-苄基羟胺 在 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide
  参考文献：
  名称：

  A Novel and Practical Synthesis of l-Hexoses from d-Glycono-1,5-lactones

  摘要：

  A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, delta-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. None of the N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into the L-sugars.

  DOI：

  10.1021/ja992808t

文献信息

• A Novel and Practical Synthesis of <scp>l</scp>-Hexoses from <scp>d</scp>-Glycono-1,5-lactones
  作者：Hideyo Takahashi、Yuko Hitomi、Yoshinori Iwai、Shiro Ikegami

  DOI：10.1021/ja992808t

  日期：2000.4.1

  A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, delta-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. None of the N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into the L-sugars.
• Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars
  作者：Hideyo Takahashi、Tomomi Shida、Yuko Hitomi、Yoshinori Iwai、Namisa Miyama、Kazusa Nishiyama、Daisuke Sawada、Shiro Ikegami

  DOI：10.1002/chem.200600268

  日期：2006.7.24

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.