(3S,4S)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid | 173355-98-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4S)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid
• 英文别名: (3s,4s)-4-beta-d-Glucopyranosyloxy-3-methyloctanoic acid；(3S,4S)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctanoic acid
• CAS: 173355-98-1
• 化学式: C₁₅H₂₈O₈
• 分子量: 336.383
• InChiKey: GXJOFLPBVXYYSQ-SXKHRBNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid 在 β-glucosidase enzyme 、 AR₂₀₀₀ enzyme 作用下， 反应 48.0h， 生成 (-)-反式威士忌内酯 、 (4R,5R)-5-丁基-4-甲基二氢呋喃-2(3H)-酮
  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：

  2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖 在 2,6-二甲基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3S,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

文献信息

• Precursors to oak lactone. Part 2: Synthesis, separation and cleavage of several β-d-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid
  作者：Kerry L Wilkinson、Gordon M Elsey、Rolf H Prager、Takashi Tanaka、Mark A Sefton

  DOI：10.1016/j.tet.2004.05.070

  日期：2004.7

  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.