2-Deoxy-2,3-O-isopropylidene-2,4-di-C-methyl-beta-L-arabinose | 1219451-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Deoxy-2,3-O-isopropylidene-2,4-di-C-methyl-beta-L-arabinose
• 英文别名: (3aS,6S,7S,7aR)-2,2,3a,7-tetramethyl-4,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol
• CAS: 1219451-02-1
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: QQTDXBQRNRMECI-ODHVRURNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Deoxy-2,3-O-isopropylidene-2,4-di-C-methyl-beta-L-arabinose 在 Dowex (50 W X₈ H⁺) 作用下， 以 水 为溶剂， 反应 1.5h， 以82%的产率得到2-deoxy-2,4-di-C-methyl-L-arabinose
  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：

  在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到2-Deoxy-2,3-O-isopropylidene-2,4-di-C-methyl-beta-L-arabinose
  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