benzyl (2S,3R,4S,5R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylate | 203632-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2S,3R,4S,5R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 203632-28-4
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: MAWQZLVRWTYLGK-RXTJHEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3R,4S,5R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylate 在 咪唑 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 benzyl (3aR,4S,7R,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-6-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-carboxylate
  参考文献：
  名称：

  Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

  摘要：

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.

  DOI：

  10.1021/jo971323p
• 作为产物：
  描述：

  氨甲酸,(2-氟环丙基)-,1,1-二甲基乙基酯,顺-(9CI) 、 苯甲醇 在 对甲苯磺酸 作用下， 反应 4.0h， 以94%的产率得到benzyl (2S,3R,4S,5R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones

  摘要：

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.

  DOI：

  10.1021/jo971323p

文献信息

• Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones
  作者：Cosme G. Francisco、Concepción González Martín、Ernesto Suárez

  DOI：10.1021/jo971323p

  日期：1998.4.1

  Alduronic acid 4,1-, 5,1-, and 5,2-lactones can be specifically obtained when hexuronic and penturonic acids belonging to the erythrose and threose carbohydrate series undergo a tandem beta-fragmentation-intramolecular cyclization reaction. In this way, gamma-lactones such as 3-O-formyl-1,2-O-isopropylidene-D-threurono-4,1-lactone (38), 3-O-formyl-1,2-di-O-methyl-D-threurono-4,1-lactones (39), or 3-O-formyl-1,2-O-isopropylidene-D-erythrurono-4,1-lactone (41), and delta-lactones such as 1-O-(tert-butyldimethylsilyl)-4-O-formyl-2,3-O-isopropylidene-D-lyxurono-5,1-lactones (40), or 4-O-formyl-1,2,3-tri-O-methyl-D-arabinurono-5,1-lactones (42), or 3-O-benzyl-4-O-formyl-1,2-O-isopropylidene-D-arabinurono-5,1-lactone (43), were obtained. Alternatively, an intermolecular reaction took place when the carboxyl group was lactonized. Thus, 1,4-di-O-acetyl-3-formyl-1-iodo-D-arabininurono-5,2-lactone (45) was prepared from 2,5-di-O-acetyl-D-glucurono-6,3-lactone (37). The reaction is promoted by two different systems: (diacetoxyiodo)benzene (DIB)-iodine, under mild conditions, or diphenylhydroxyselenium acetate (DHSA)-iodine under visible light irradiation. With this new strategy, nor-aldopyranosuronic and aldofuranosuronic acid lactones are formed via 1,5 and 1,6 intramolecular cyclization.