2,5-di-O-acetyl-D-glucofuranurono-6,3-lactone | 110157-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2,5-di-O-acetyl-D-glucofuranurono-6,3-lactone
• 英文别名: [(3R,3aS,6S,6aS)-6-acetyloxy-2-hydroxy-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-3-yl] acetate
• CAS: 110157-33-0
• 化学式: C₁₀H₁₂O₈
• 分子量: 260.2
• InChiKey: XFPVLGAKWCMXRB-FHDFAIOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,5-di-O-acetyl-D-glucofuranurono-6,3-lactone 在 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以67%的产率得到Acetic acid (3S,4R,5S)-5-(acetoxy-iodo-methyl)-4-formyloxy-2-oxo-tetrahydro-furan-3-yl ester
  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：

  1-O-benzyl-α-D-glucofuranurono-6,3-lactone 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 39.0h， 生成 2,5-di-O-acetyl-D-glucofuranurono-6,3-lactone
  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

• O-pivaloyl-d-glucofuranurono-6,3-lactones: Use of the pivaloyl group for positional assignments of substituents in the sugar ring
  作者：Dina Keglević、Djurdjica Ljevaković、Srdanka Tomić-Kulenović

  DOI：10.1016/s0008-6215(00)85981-9

  日期：——
• Synthesis of α-Iodoalkyl Esters and α-Iodoalkyl Carbonates from Carbohydrates. Formation of Convenient Chiral Synthetic Intermediates
  作者：Cosme G. Francisco、Concepción González Martín、Ernesto Suárez

  DOI：10.1021/jo981587r

  日期：1998.11.1
• 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.