(1R)-1-[(4R,5S)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol | 126147-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(4R,5S)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 126147-48-6
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: ZSHYYJOMEOZLKL-BHNWBGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(4R,5S)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以100%的产率得到2,3-O-isopropylidene-3-C-methyl-L-erythrpfuranose
  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：

  2,3-O-异丙亚基-2-C-甲基-D-核糖酸-gamma-内酯 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以100%的产率得到(1R)-1-[(4R,5S)-5-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
  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

文献信息

• ANDO, KENSHI;YAMADA, TAKAO;SHIBUYS, MASAYUKI, HETEROCYCLES, 29,(1989) N1, C. 2209-2218
  作者：ANDO, KENSHI、YAMADA, TAKAO、SHIBUYS, MASAYUKI

  DOI：——

  日期：——