1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol | 55491-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol
• 英文别名: (2R,3R,4S,5S)-4,5-dimethoxy-2-(methoxymethyl)oxan-3-ol
• CAS: 55491-50-4
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: FSHQSETZFKFJAM-BZNPZCIMSA-N

物化性质

• 沸点：
  303.0±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol 以 吡啶 为溶剂， 反应 1.0h， 以80%的产率得到4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol
  参考文献：
  名称：

  Analysis of linkage positions in d-glucopyranosyl residues by the reductive-cleavage method

  摘要：

  DOI：

  10.1016/0008-6215(85)85159-4
• 作为产物：
  描述：

  甲基2,3,6-三-O-甲基-alpha-D-吡喃葡萄糖苷 在 三甲基硅基甲烷磺酸酯 、 三氟化硼乙醚 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以16 mg的产率得到1,5-anhydro-2,3,6-tri-O-methyl-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

文献信息

• Characterization of cyclomalto-hexaose and -heptaose derivatives by the reductive-cleavage method
  作者：Petra Mischnick-Lübbecke、Ralph Krebber

  DOI：10.1016/0008-6215(89)80003-5

  日期：1989.4

  The substitution patterns of cyclomalto-hexaose and -heptaose derivatives carrying alkyl, acyl, and carbamoyl substituents have been investigated by the reductive-cleavage method. The modified cyclomalto-hexaoses or -heptaoses were treated with triethylsilane and trimethylsilyl trifluoromethanesulfonate to give the corresponding 1,5- and 1,4-anhydroglucitol derivatives that were acetylated or, in the

  摘要：通过还原裂解方法研究了带有烷基，酰基和氨基甲酰基取代基的环麦芽六糖和庚糖衍生物的取代方式。用三乙基硅烷和三甲基甲硅烷基三氟甲磺酸酯处理改性的环麦芽六糖或庚二酮酶，得到相应的1,5-和1,4-脱水葡萄糖醇衍生物，将其乙酰化，或在乙酰基衍生物的情况下，将三氟乙酰基化，并通过glc-ms分析可以检测到烷基化化合物，烷基化不足或烷基化形成的微量产物或异构体组分。观察到酰氧基部分还原为烷氧基和酰基取代基的裂解。氨基甲酰基取代基在还原裂解的条件下是稳定的。
• Transglycosylation reactions of permethylated methyl d-glucopyranosides with partially methylated 1,5-anhydroalditols
  作者：Chang Kiu Lee、Eun Ju Kim

  DOI：10.1016/0008-6215(95)00290-1

  日期：1996.1

  Transglycosylation of methyl 2,3,4,6-tetra-O-methyl-alpha- and beta-D-glucopyranosides with 1,5-anhydro-2,3,6-tri-O-methyl-D-glucitol and 1,5-anhydro-2,3,4-tri-O-methyl-D-glucitol took place in the presence of trimethylsilyl trifluoromethanesulfonate or boron trifluoride etherate, resulting in the formation of disaccharide derivatives. A disaccharide which could have been formed by the transglycosylation

  甲基2,3,4,6-四-O-甲基-α-和β-D-吡喃葡萄糖苷与1,5-脱水-2,3,6-三-O-甲基-D-葡萄糖醇和1，在三甲基甲硅烷基三氟甲磺酸盐或三氟化硼醚化物的存在下发生5-脱水-2,3,4-三-O-甲基-D-葡萄糖醇，导致形成二糖衍生物。在过甲基化支链淀粉的还原裂解反应中观察到了可能由中间体的转糖基化反应形成的二糖。
• Studies of model compounds for the analysis of ester-containing polysaccharides by the reductive-cleavage method
  作者：Judith S. Sherman、Gary R. Gray

  DOI：10.1016/0008-6215(92)84021-j

  日期：1992.7

  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.
• Analysis of linkage positions in d-glucopyranosyl residues by the reductive-cleavage method
  作者：David Rolf、John A. Bennek、Gary R. Gray

  DOI：10.1016/0008-6215(85)85159-4

  日期：1985.3