5-Hydroxymethyl-3,3-dimethoxy-2-methyl-tetrahydrofuran | 15358-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Hydroxymethyl-3,3-dimethoxy-2-methyl-tetrahydrofuran
• 英文别名: (+/-)-2-Methyl-3,3-dimethoxy-5-hydroxy-methyl-tetrahydrofuran；(4,4-Dimethoxy-5-methyloxolan-2-yl)methanol
• CAS: 15358-07-3
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: WUOOMJSTTFTWGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Hydroxymethyl-3,3-dimethoxy-2-methyl-tetrahydrofuran 在 dipotassium hydrogenphosphate 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 sodium iodide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 27.5h， 生成 (-)-allo-muscarine iodide
  参考文献：
  名称：

  Chemoenzymic synthesis of the eight stereoisomeric muscarines

  摘要：

  Efficient syntheses of the eight stereoisomers of muscarine have been accomplished by dehydrogenase-catalyzed reduction of iodo ketones (+/-)-3a and (+/-)-3b. 3-alpha,20-beta-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans exhibited high enantiomeric and diastereotopic selectivity for (+/-)-3a, yielding an equimolar mixture of iodo alcohol (-)-4 (2S,4S,5S) (96% ee) and iodo ketone (+)-3a (2R,5R) (96% ee) which was reduced by sodium borohydride to a mixture of (+)-4 and (+)-5. 3-beta,17-beta-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni reduced (+/-)-3b with high diastereotopic selectivity to give an equimolar mixture of iodo alcohols (+)-6 (2R,4S,5S) (> 99% ee) and (-)-7 (2S,4S,5R) (81% ee). Synthesis of the remaining iodo alcohols [(-)-5, (-)-6, and (+)-7] was achieved by applying the Mitsunobu procedure to (-)-4, (-)-7, and (+)-6. The enantiomeric excess of intermediates 4-7 was determined by HPLC analysis of the (R)-(+)-MTPA esters. The chiral iodo alcohols 4-7 were then transformed into the final derivatives by conventional chemical manipulations.

  DOI：

  10.1021/jo00001a015
• 作为产物：
  描述：

  4,4-Dimethoxy-5-methyl-tetrahydro-furan-2-carbonsaeure-methylester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到5-Hydroxymethyl-3,3-dimethoxy-2-methyl-tetrahydrofuran
  参考文献：
  名称：

  Chemoenzymic synthesis of the eight stereoisomeric muscarines

  摘要：

  Efficient syntheses of the eight stereoisomers of muscarine have been accomplished by dehydrogenase-catalyzed reduction of iodo ketones (+/-)-3a and (+/-)-3b. 3-alpha,20-beta-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans exhibited high enantiomeric and diastereotopic selectivity for (+/-)-3a, yielding an equimolar mixture of iodo alcohol (-)-4 (2S,4S,5S) (96% ee) and iodo ketone (+)-3a (2R,5R) (96% ee) which was reduced by sodium borohydride to a mixture of (+)-4 and (+)-5. 3-beta,17-beta-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni reduced (+/-)-3b with high diastereotopic selectivity to give an equimolar mixture of iodo alcohols (+)-6 (2R,4S,5S) (> 99% ee) and (-)-7 (2S,4S,5R) (81% ee). Synthesis of the remaining iodo alcohols [(-)-5, (-)-6, and (+)-7] was achieved by applying the Mitsunobu procedure to (-)-4, (-)-7, and (+)-6. The enantiomeric excess of intermediates 4-7 was determined by HPLC analysis of the (R)-(+)-MTPA esters. The chiral iodo alcohols 4-7 were then transformed into the final derivatives by conventional chemical manipulations.

  DOI：

  10.1021/jo00001a015