(3R,4S)-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoic acid | 741717-03-3

• 英文名称: (3R,4S)-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoic acid
• CAS: 741717-03-3
• 化学式: C₃₅H₆₀O₁₂
• 分子量: 672.854
• InChiKey: YSEDRXIMIJPGSZ-DEBOHWDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  160.96
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoic acid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以100%的产率得到(3R,4S)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid
  参考文献：
  名称：

  Precursors to oak lactone. Part 2: Synthesis, separation and cleavage of several β-d-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid

  摘要：

  The beta-D-glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared. The (3S,4S) and (3R,4R) species were prepared from cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (cis-oak lactone) by a process involving ring-opening with base and protection of the carboxyl function as its benzyl ester. The glucose unit was introduced by a modified Koenigs-Knorr procedure. A different strategy was necessary for synthesis of the (3S,4R) and (3R,4S) compounds. This was based on the reductive ring-opening of trans-oak lactone and subsequent protection of the primary alcohol as its t-butyldiphenylsilyl ether. Separation of the individual glucosides was effected by preparative thin layer chromatography. Those corresponding to the nature-identical isomers of oak lactone have been shown to produce oak lactone under both acidic hydrolysis and pyrolysis conditions. The galloyl-beta-D-glucoside of the cis-species, obtained as a natural isolate from the wood of Platycarya strobilacea, was also found to produce cis-oak lactone upon both acid hydrolysis and pyrolysis. Both the nature-identical (4S,5S) cis-oak lactone and its non-natural (4R,5R) enantiomer have been prepared from their corresponding glycosides and their aroma thresholds in white wine were determined to be 23 and 82 mug/L (ppb) respectively. The aroma threshold of the nature-identical isomer in a red wine was 46 mug/L. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.070
• 作为产物：
  描述：

  (3R,4S)-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以87.0 mg的产率得到(3R,4S)-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoic acid
  参考文献：
  名称：

  Precursors to oak lactone. Part 2: Synthesis, separation and cleavage of several β-d-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid

  摘要：

  The beta-D-glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared. The (3S,4S) and (3R,4R) species were prepared from cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (cis-oak lactone) by a process involving ring-opening with base and protection of the carboxyl function as its benzyl ester. The glucose unit was introduced by a modified Koenigs-Knorr procedure. A different strategy was necessary for synthesis of the (3S,4R) and (3R,4S) compounds. This was based on the reductive ring-opening of trans-oak lactone and subsequent protection of the primary alcohol as its t-butyldiphenylsilyl ether. Separation of the individual glucosides was effected by preparative thin layer chromatography. Those corresponding to the nature-identical isomers of oak lactone have been shown to produce oak lactone under both acidic hydrolysis and pyrolysis conditions. The galloyl-beta-D-glucoside of the cis-species, obtained as a natural isolate from the wood of Platycarya strobilacea, was also found to produce cis-oak lactone upon both acid hydrolysis and pyrolysis. Both the nature-identical (4S,5S) cis-oak lactone and its non-natural (4R,5R) enantiomer have been prepared from their corresponding glycosides and their aroma thresholds in white wine were determined to be 23 and 82 mug/L (ppb) respectively. The aroma threshold of the nature-identical isomer in a red wine was 46 mug/L. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.070