methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside | 32453-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside
• 英文别名: methyl-2,3,4-tri-O-acetyl-α-D-arabinopyranoside；methyl-[tri-O-acetyl-α-D-arabinopyranoside；Methyl-[tri-O-acetyl-α-D-arabinopyranosid；Methyl-tri-O-acetyl-α-D-arabinopyranosid；Methyl-α-D-arabinopyranosid-triacetat；(2S,3S,4R,5R)-2-Methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate；[(3R,4R,5S,6S)-4,5-diacetyloxy-6-methoxyoxan-3-yl] acetate
• CAS: 32453-58-0
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: YBESHGJFPWHRBW-WYUUTHIRSA-N

物化性质

• 沸点：
  332.1±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 溶剂黄146 、 (E)-3-Ureido-but-2-enoic acid ethyl ester 、 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Crystalline Acetal Derivatives of d-Arabinose¹

  摘要：

  DOI：

  10.1021/ja01285a049
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R)-2,3-diacetoxy-5-formyloxy-tetrahydro-pyran-4-yl ester 生成 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside
  参考文献：
  名称：

  ICHIKAWA, SHUJI;TOMITA, ISAO;HOSAKA, AKIRA;SATO, TADASHI, BULL. CHEM. SOC. JAP., 61,(1988) N 2, 513-520

  摘要：

  DOI：

文献信息

• Methyltrioxorhenium-Catalyzed Epoxidation-Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions
  作者：Andrea Goti、Francesca Cardona、Gianluca Soldaini、Claudia Crestini、Cinzia Fiani、Raffaele Saladino

  DOI：10.1002/adsc.200505412

  日期：2006.3

  The efficient and high yielding domino epoxidation-methanolysis of glycals 8–15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16–23a, b by direct acetylation of the crude mixtures. Homogeneous MTO-amine complexes 5–7, heterogeneous poly(4-vinylpyridine)/MTO compounds I–III, and microencapsulated polystyrene/MTO

  高效和高产多米诺烯糖的环氧化-甲醇8 - 15已被氧化，UHP在MeOH实现催化由MTO。该产品已被方便地分离为2-乙酰氧基衍生物16 - 23A，B通过将粗混合物直接乙酰化。均质MTO -胺络合物5 - 7，异构聚（4-乙烯基吡啶）/ MTO化合物我- III，和微囊化聚苯乙烯/ MTO系统IV - VII还测试并证明了它们作为氧化步骤催化剂的有效性。取决于基质，氧化的表面非对映选择性从令人满意的到优异的，并且可以通过充分筛选催化剂来优化。在环境友好的实验条件下，使用简单的后处理程序即可获得底物的完全转化和近乎定量的产品收率。
• Conformational studies on pyranoid sugar derivatives by n.m.r. spectroscopy. Conformational equilibria of the peracetylated and some perbenzoylated methyl d-aldopentopyranosides in solution
  作者：P.L. Durette、D. Horton

  DOI：10.1016/s0008-6215(00)80276-1

  日期：1971.7

  used to determine by n.m.r. spectroscopy the conformational populations of the eight methyl d -aldopentopyranoside triacetates and the corresponding tribenzoates having the β- d - ribo , β- d - arabino , α- d - xylo , β- d - xylo , and α- d - lyxo configurations. The α- d - xylo derivatives adopt the C1 ( d ) conformation almost exclusively, and the β- d - arabino derivatives favor the 1C ( d ) conformation

  摘要采用平均自旋偶合方法，通过核磁共振波谱法测定了8种甲基d-醛糖醛糖吡喃糖苷三乙酸酯和相应的具有β-d-核糖，β-d-阿拉伯糖，α-d-木糖基的三苯甲酸酯的构象种群。 ，β-d-xylo和α-d-lyxo构型。α-d-xylo衍生物几乎完全采用C1（d）构象，而β-d-arabino衍生物非常倾向于1C（d）构象。在解决方案中，其他示例都具有相当比例的两个椅子构造者。除了当轴向1-取代基与3-取代基同轴时，C-1处甲氧基的轴向导向作用大于乙酰氧基或苯甲酰氧基的轴向导向作用。通过用苯甲酰氧基取代C-2、3和4上的乙酰氧基，可以增强C-1上甲氧基的轴向定向作用。根据极性和空间贡献来讨论1-取代基的轴向作用。对于甲基2,3,4-三-O-苯甲酰基-β-d-吡喃吡喃糖苷，发现全轴椅子构象异构体的比例随着溶剂极性的增加而降低；这种行为与一些醛戊糖基吡喃糖四乙酸盐和三-O-乙酰基-β-d-吡喃吡喃糖基
• Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate
  作者：Innaiah K. Polanki、Siva H. Kurma、Asish K. Bhattacharya

  DOI：10.1080/07328303.2015.1028585

  日期：2015.5.4

  Bi(NO3)(3), a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
• Rusavskaya, T. N.; Studentsov, E. P.; Sokolov, V. M., Journal of general chemistry of the USSR, 1983, vol. 53, # 2, p. 380 - 388
  作者：Rusavskaya, T. N.、Studentsov, E. P.、Sokolov, V. M.、Zakharov, V. I.、Ivanov, M. A.

  DOI：——

  日期：——