2,3-di-C-methyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone | 952431-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-C-methyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone
• 英文别名: 2,4-Dimethyl-3,4-O-isopropylidene-L-arabinono lactone；(3aS,7R,7aR)-7-hydroxy-2,2,3a,7-tetramethyl-4,7a-dihydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 952431-72-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: OXXGADUHBQUBHW-JMOVZRAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di-C-methyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以67%的产率得到
  参考文献：
  名称：

  Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

  摘要：

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.098
• 作为产物：
  描述：

  sodium cyanide 、 (3aS,6aS)-2,2,3a,6-tetramethyl-4,6a-dihydrofuro[3,4-d][1,3]dioxol-6-ol 以 水 为溶剂， 以77%的产率得到2,3-di-C-methyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone
  参考文献：
  名称：

  Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

  摘要：

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.098