1,2-O-isopropylidene-5-O-methoxycarbonyl-α-D-ribofuranoside | 1388091-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-methoxycarbonyl-α-D-ribofuranoside
• 英文别名: [(3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl methyl carbonate
• CAS: 1388091-99-3
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: GGDOHLQEKFUTGN-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-methoxycarbonyl-α-D-ribofuranoside 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以82%的产率得到1,2-O-isopropylidene-3,5-O-di(methoxycarbonyl)-α-D-ribofuranoside
  参考文献：
  名称：

  Alkyloxycarbonyl group migration in furanosides

  摘要：

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.117
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1,2-O-isopropylidene-5-O-methoxycarbonyl-α-D-ribofuranoside 、 1,2-O-isopropylidene-3-O-methylcarbonate-α-D-ribofuranose 、 1,2-O-isopropylidene-3,5-O-di(methoxycarbonyl)-α-D-ribofuranoside 、 bis(1,2-O-isopropylidene-α-D-ribofuranoside)-3-carbonate
  参考文献：
  名称：

  Alkyloxycarbonyl group migration in furanosides

  摘要：

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.117

文献信息

• Alkyloxycarbonyl group migration in furanosides
  作者：Marcela Dvorakova、Marie Pribylova、Radek Pohl、Marie E. Migaud、Tomas Vanek

  DOI：10.1016/j.tet.2012.05.117

  日期：2012.8

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.