2,3,4,6-tetra-O-benzyl-L-idono-1,5-lactone | 222416-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-L-idono-1,5-lactone
• 英文别名: 2,3,4,6-tetra-O-benzyl-L-gulonolactone；(3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 222416-53-7
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: BUBVLQDEIIUIQG-ISSPZXTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-L-idono-1,5-lactone 在 magnesium iodide 作用下， 以 乙醇-D1 为溶剂， 反应 1.0h， 以98%的产率得到2,4,6-tri-O-benzyl-3-deoxy-L-erythro-hex-2-enone-1,5-lactone
  参考文献：
  名称：

  C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization

  摘要：

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.10.006
• 作为产物：
  描述：

  5-内酯 在 三甲基铝 、 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 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.67h， 生成 2,3,4,6-tetra-O-benzyl-L-idono-1,5-lactone
  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

• Intramolecular Tishchenko Reactions of Protected Hexos-5-uloses: a Novel and Efficient Synthesis of l-Idose and l-Altrose
  作者：M. Adinolfi、G. Barone、F. De Lorenzo、A. Iadonisi

  DOI：10.1055/s-1999-3156

  日期：1999.3

  Protected t-butyl esters of aldonic acids with the rare L-ido and L-altro configuration can be effectively obtained by a diastereoselective Tishchenko reaction of hexos-5-uloses induced by t-BuOSmI2. These compounds can be easily converted into the corresponding protected lactones and free sugars.

  可以通过t-BuOSmI2诱导的六碳糖5-酮糖的立体选择性Tishchenko反应，有效地获得具有稀有L-ido和L-altro构象的戊酸的保护叔丁基酯。这些化合物可以容易地转化为相应的保护内酯和游离糖。
• 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.
• C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
  作者：Julie Gratien、Marie-Pierre Heck、Charles Mioskowski

  DOI：10.1016/j.carres.2007.10.006

  日期：2008.1

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.