(3aR,6R,6aR)-3a,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one | 68124-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6R,6aR)-3a,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one
• CAS: 68124-03-8
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: POJKBDAWSCJRPD-HCVRKRLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aR)-3a,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydrofuro[3,4-d][1,3]dioxol-4-one 在 二甲基氯化铝 、 4-甲基苯磺酸吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.41h， 生成 (-)-(3aR,6aR)-3a-(hydroxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)one
  参考文献：
  名称：

  Synthesis of (+)/(−) pentenomycins via Me2AlCl induced cascade reaction

  摘要：

  An efficient approach for the synthesis of (+) pentenomycin and (-) pentenomycin from D-ribose and D-mannose, respectively, is described using Tebbe olefination of lactones 9 and 7 followed by Me2AlCl induced disfavoured 5-(enol-endo)-exo-trig cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.092

文献信息

• High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent
  作者：Daniel Best、Sarah F. Jenkinson、Sebastian D. Rule、Rosemary Higham、Thomas B. Mercer、Richard J. Newell、Alexander C. Weymouth-Wilson、George W.J. Fleet、Sigthor Petursson

  DOI：10.1016/j.tetlet.2008.02.042

  日期：2008.3

  can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene;

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。
• Synthesis of (+)/(−) pentenomycins via Me2AlCl induced cascade reaction
  作者：Bejugam Santhosh Kumar、Girija Prasad Mishra、Batchu Venkateswara Rao

  DOI：10.1016/j.tetlet.2013.03.092

  日期：2013.5

  An efficient approach for the synthesis of (+) pentenomycin and (-) pentenomycin from D-ribose and D-mannose, respectively, is described using Tebbe olefination of lactones 9 and 7 followed by Me2AlCl induced disfavoured 5-(enol-endo)-exo-trig cyclization. (C) 2013 Elsevier Ltd. All rights reserved.