tert-Butyl-{(R)-2-methoxy-2-[(3aS,4R,6S,6aS)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethoxy}-dimethyl-silane | 203632-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-Butyl-{(R)-2-methoxy-2-[(3aS,4R,6S,6aS)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethoxy}-dimethyl-silane
• 英文别名: [(2R)-2-[(3aS,4S,6R,6aS)-4-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-methoxyethoxy]-tert-butyl-dimethylsilane
• CAS: 203632-43-3
• 化学式: C₂₄H₄₀O₇Si
• 分子量: 468.663
• InChiKey: XSOCBYBDTCQKGP-AANPDWTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-Butyl-{(R)-2-methoxy-2-[(3aS,4R,6S,6aS)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethoxy}-dimethyl-silane 在 氟化铵 、 重铬酸吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 p-methoxybenzyl 2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranosiduronic acid
  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：

  2,3-O-isopropylidene-1-O-p-methoxybenzyl-α-D-mannofuranoside 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 tert-Butyl-{(R)-2-methoxy-2-[(3aS,4R,6S,6aS)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethoxy}-dimethyl-silane
  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.