1,5-anhydro-3,4,6-tri-O-methyl-2-O-propionyl-D-glucitol | 143835-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-3,4,6-tri-O-methyl-2-O-propionyl-D-glucitol
• CAS: 143835-59-0
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: QRLAEOCLCUQCAE-RBLKWDMZSA-N

反应信息

• 作为产物：
  描述：

  methyl 3,4,6-tri-O-methyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 吡啶 、 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,5-anhydro-3,4,6-tri-O-methyl-2-O-propionyl-D-glucitol
  参考文献：
  名称：

  Studies of model compounds for the analysis of ester-containing polysaccharides by the reductive-cleavage method

  摘要：

  The four O-propionyl regioisomers of methyl tri-O-methyl-alpha-D-glucopyranoside and the 2- and 3-O-propionyl regioisomers of methyl tri-O-methyl-beta-D-glucopyranoside were subjected to reductive cleavage in the presence of Et3SiH and Me3SiOSO2CF3, BF3.Et2O, or Me3SiOSO2Me-BF3.Et2O. The O-propionyl group was stable when either Me3SiOSO2CF3 or BF3.Et2O Was the catalyst, but was slowly reduced to the (1-propyl) ether when Me3SiOSO2Me-BF3.Et2O was the catalyst. Reductive cleavages catalyzed by Me3SiOSO2CF3 were complete in 6 h, those catalyzed by BF3.Et2O required at least 24 h, and those catalyzed by Me3SiOSO2Me-BF3.Et2O required 30 min or less. In the alpha-series, the rate of reductive cleavage decreased in the order 6-O-propionyl > 4-O-propionyl > 3-O-propionyl much greater than 2-O-propionyl. The reductive cleavage of beta-anomers was faster than that of the corresponding alpha-anomers. This effect was particularly striking for the alpha and beta-anomers of the 2-O-propionyl regioisomer, as would be expected on the basis of a participation reaction.

  DOI：

  10.1016/0008-6215(92)84021-j