1,3,4-tri-O-acetyl-β-L-arabinopyranose | 135593-77-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4-tri-O-acetyl-β-L-arabinopyranose
• 英文别名: 1,3,4-triacetyl-α-D-xylopyranose；[(3S,4R,5R,6R)-4,6-diacetyloxy-5-hydroxyoxan-3-yl] acetate
• CAS: 135593-77-0
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: MEIQBWLBEHTALO-ZRUFSTJUSA-N

物化性质

• 熔点：
  101-102.5 °C
• 沸点：
  352.2±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-acetyl-β-L-arabinopyranose 在 水 、 乙酸酐 、 potassium carbonate 、 二甲基亚砜 作用下， 以 水 、 乙腈 为溶剂， 反应 114.0h， 生成 3,4-dimethoxy-N-methylpyridinium iodide
  参考文献：
  名称：

  Dehmlow, Eckehard V.; Westerheide, Ralf, Heterocycles, 1994, vol. 37, # 1, p. 355 - 366

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-di-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-L-arabinopyranose 在 溶剂黄146 作用下， 反应 0.25h， 以33.5%的产率得到1,3,4-tri-O-acetyl-β-L-arabinopyranose
  参考文献：
  名称：

  A new stereospecific method for 1,2-cis-glycosylation

  摘要：

  A new stereospecific method for 1,2-cis-glycosylation involves the reaction of 1,2-trans-glycosyl thiocyanates with sugar trityl ethers in the presence of triphenylmethylium perchlorate, The method has been applied to give disaccharide derivatives with (1 --> 6), (1 --> 4),(1 --> 3), and (1 --> 2) linkages.

  DOI：

  10.1016/0008-6215(91)84047-i

文献信息

• Stereoselective Ring-Opening of Acetylated Pyranose-1,2-(etyl orthoacetates).
  作者：Setsuo SAITO、Shigeya SUMITA、Koki ICHINOSE、Yasuhiko KANDA

  DOI：10.1248/cpb.41.90

  日期：——

  When acetylated pyranose-1, 2-(ethyl orthyl orthoacetates) were hydrolyzed in acidic solvents, the ring-opening of the orthoacetate rings was influenced by the axial or equatorial OAc group at C-4 on the pyranoses; on acid-catalyzed hydrolysis, 3, 4, 6-tri-O-acetyl-α-D-glactopyranose- (8) and methyl 3, 4-di-O-acetyl-α-D-galacturonatopyranose-1, 2-(ethyl orthoacetate) (16) having an axial OAc group at C-4 on the pyranose rings gave 1, 3, 4, 6-tetra-O-acetyl-α-D-galactopyranose (9) and methyl 1, 3, 4-tri-O-acetyl-α-D-galacturonatopyranose (23), respectively, whereas 3, 4, 6-tri-O-acetyl-α-D-glucopyranose- (10) and methyl 3, 4-di-O-acetyl-α-D-glucuronatopyranose-1, 2-(ethyl orthoacetate) (22)having an equatorial OAc group at C-4 on the pyranose rings gave 2, 3, 4, 6-tetra-O-acetyl-D-glucopyranose (11) and methyl 2, 3, 4-tri-O-acetyl-D-glucuronatopyranose (24), respectively. On the acid-catalyzed hydrolysis, 3, 4-di-O-acetyl-β-L-arabinopyranose-1, 2-(ethyl orthoacetate) (34) having an axial OAc group at C-4 on the pyranose ring gave a mixture of 1, 3, 4-tri-O-acetyl-β-L- (35) and 2, 3, 4-tri-O-acetyl-L-arabinopyranose (36). These selectivities of ring-opening of the 1, 2-(orthoacetates) were considered to have resulted from the differences of the conformers fo the 1, 2-(orthoacids)intermediates derived from the 1, 2-(othoacetates) and the orientation of the acetyl groups at C-4 on the pyranose rings.

  当乙酰化的吡喃糖1,2-(乙基邻酸酯)在酸性溶剂中水解时，邻酸酯环的开环受吡喃糖C-4位点的轴向或赤道OAc基团的影响；在酸催化水解过程中，具有C-4轴向OAc基团的3,4,6-三-O-乙酰-α-D-半乳糖吡喃糖-(8)和甲基3,4-二-O-乙酰-α-D-半乳糖酸吡喃糖-1,2-(乙基邻酸酯)(16)分别生成1,3,4,6-四-O-乙酰-α-D-半乳糖吡喃糖(9)和甲基1,3,4-三-O-乙酰-α-D-半乳糖酸吡喃糖(23)，而具有C-4赤道OAc基团的3,4,6-三-O-乙酰-α-D-葡萄糖吡喃糖-(10)和甲基3,4-二-O-乙酰-α-D-葡萄糖醛酸吡喃糖-1,2-(乙基邻酸酯)(22)则分别生成2,3,4,6-四-O-乙酰-D-葡萄糖吡喃糖(11)和甲基2,3,4-三-O-乙酰-D-葡萄糖醛酸吡喃糖(24)。在酸催化水解过程中，具有C-4轴向OAc基团的3,4-二-O-乙酰-β-L-阿拉伯糖吡喃糖-1,2-(乙基邻酸酯)(34)生成1,3,4-三-O-乙酰-β-L-(35)和2,3,4-三-O-乙酰-L-阿拉伯糖吡喃糖(36)的混合物。这些1,2-(邻酸酯)的开环选择性被认为是由1,2-(邻酸)中间体的构象差异以及吡喃糖环上C-4位置的乙酰基团的取向所导致的。
• KOCHETKOV, NICOLAY K.;KLIMOV, EVGENY M.;MALYSHEVA, NELLY N.;DEMEHENKO, AL+, CARBOHYDR. RES., 212,(1991) C. 77-91
  作者：KOCHETKOV, NICOLAY K.、KLIMOV, EVGENY M.、MALYSHEVA, NELLY N.、DEMEHENKO, AL+

  DOI：——

  日期：——