3,4,6-tri-O-benzyl-β-D-mannopyranose | 911291-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-β-D-mannopyranose
• 英文别名: 3,4,6-tri-O-benzyl-α-D-mannose；(2R,3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2,3-diol
• CAS: 911291-36-6
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: IAEIBZGLRQJURL-UDLFFNGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-β-D-mannopyranose 在 吡啶 、 碳酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Mayer, Thomas G.; Kratzer, Bernd; Schmidt, Richard R., Angewandte Chemie, 1994, vol. 106, # 21, p. 2289 - 2293

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 在 sodium hydride 、 溶剂黄146 作用下， 生成 3,4,6-tri-O-benzyl-β-D-mannopyranose
  参考文献：
  名称：

  Mayer, Thomas G.; Kratzer, Bernd; Schmidt, Richard R., Angewandte Chemie, 1994, vol. 106, # 21, p. 2289 - 2293

  摘要：

  DOI：

文献信息

• Total Synthesis of Everninomicin 13,384-1-Part 4: Explorations of Methodology; Stereocontrolled Synthesis of 1,1′-Disaccharides, 1,2-Seleno Migrations in Carbohydrates, and Solution- and Solid-Phase Synthesis of 2-Deoxy Glycosides and Orthoesters
  作者：K. C. Nicolaou、Konstantina C. Fylaktakidou、Helen J. Mitchell、Floris L. van Delft、Rosa Maria Rodríguez、Scott R. Conley、Zhendong Jin

  DOI：10.1002/1521-3765(20000901)6:17<3166::aid-chem3166>3.0.co;2-z

  日期：——

  2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1'-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides

  报道了立体控制1,1'-二糖，2-脱氧糖苷和原酸酯的构建方法。具体而言，锡-乙缩醛部分用于固定碳水化合物受体的异头立体化学，导致1,1'-二糖的高效和立体选择性合成，而碳水化合物中新发现的1,2-苯基硒代迁移反应使2的条目打开-脱氧糖苷和原酸酯。因此，2-羟基苯基硒代糖苷与DAST的反应产生了2-苯基硒代糖基氟化物，其与碳水化合物受体反应以选择性地立体生成2-苯基硒代糖苷。后面的化合物可以通过相应的乙烯酮缩醛还原性地选择为2-脱氧糖苷或氧化转化为原酸酯。
• β-Glycosides of Hydroxyproline via an Umpolung Approach
  作者：Karl J. Shaffer、Carol M. Taylor

  DOI：10.1021/ol061424m

  日期：2006.8.1

  Reaction of 1,2-O-dibutylstannylene-3,4-6-tri-O-benzyl-beta-D-mannopyranose with N alpha-fluorenylmethoxycarbonyl-cis-4-trifluoromethanesulfonyloxyproline allyl ester led to formation of beta-mannoside of trans-4-hydroxyproline. Subsequent manipulation of the C2 hydroxy group gave rise to beta-D-Glc and beta-D-GlcNAc derivatives.
• JP5658167
  申请人：——

  公开号：——

  公开（公告）日：——
• Facile synthesis of sugar lactols via bromine-mediated oxidation of thioglycosides
  作者：Shuai Meng、Bishwa Raj Bhetuwal、Padam P. Acharya、Jianglong Zhu

  DOI：10.1080/07328303.2019.1581889

  日期：2019.2.12

  Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccinimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.[GRAPHICS].