2,3,4,6-Tetra-O-benzyl-L-gulono-1,5-lactone | 191165-35-2

• 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-gulono-1,5-lactone
• 英文别名: (3S,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 191165-35-2
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: BUBVLQDEIIUIQG-YGXYGYJOSA-N

物化性质

• 沸点：
  677.7±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

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-gulono-1,5-lactone 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 以99%的产率得到2,3,4,6-Tetra-O-benzyl-D-glucopyranose
  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：

  2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 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-gulono-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

• Cyclization Dichotomy of D-xylo-Hex-5-ulosonamides and Synthesis of Piperidine Analogs of Aldohexoses and Aldohexono-1,5-lactones
  作者：Radka Kováříková、Miroslav Ledvina、David Šaman

  DOI：10.1135/cccc19990673

  日期：——

  The preparation of 2,3,4,6-tetra-O-benzyl-5-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino- 2,3,4,6-tetra-O-benzyl-5-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (9), and also their direct transformation into 2,3,4,6-tetra-O-benzyl- D-talono-1,5-lactone (6), are described and discussed. The atypical boat conformation of D-talonolactam 5 and D-talonolactone 6 was found.

  2,3,4,6-四O-苄基-5-D-木糖-己-5-乌洛磺酰胺3a和3b的制备以及它们环化为5-氨基-2,3,4,6-四O-苄基-5-脱氧-D-葡萄糖酮-1,5-内酯(4)和5-氨基-2,3,4,6-四O-苄基-5-脱氧-D-他糖酮-1,5-内酯(5)或2,3,4,6-四O-苄基-1,5-二脱氧-1,5-亚胺-D-葡萄糖醇(9)，以及它们直接转化为2,3,4,6-四O-苄基-D-他糖-1,5-内酯(6)，被描述和讨论。发现了D-他糖内酯5和D-他糖内酯酮6的非典型舟型构象。
• Monthiller, Sophie; Heck, Marie-Pierre; Mioskowski, Charles, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 2, p. 145 - 152
  作者：Monthiller, Sophie、Heck, Marie-Pierre、Mioskowski, Charles、Lafargue, Pierre、Lellouche, Jean-Paul、Masella, Michel

  DOI：——

  日期：——
• 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.