(4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester | 150843-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (4R,5S,6R)-4-hydroxy-2-methoxy-6-methyl-5-phenylmethoxyoxane-2-carboxylate
• CAS: 150843-05-3
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: UFBCFABYPQKVGF-FLYGSYRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R,5R,6R)-4,5-bis(benzyloxy)-2-(((4R,5R,6R)-5-(benzyloxy)-2-carboxy-2-methoxy-6-methyltetrahydro-2H-pyran-4-yl)oxy)-6-methyltetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide

  摘要：

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.

  DOI：

  10.1016/s0040-4039(00)79162-3
• 作为产物：
  描述：

  (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 以62%的产率得到(4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide

  摘要：

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.

  DOI：

  10.1016/s0040-4039(00)79162-3

文献信息

• Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide
  作者：David Crich、Frank Hermann

  DOI：10.1016/s0040-4039(00)79162-3

  日期：1993.5

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.