(+)-(2R,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran | 129170-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2R,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran
• 英文别名: (2S,3R,5R)-5-(iodomethyl)-2-methyloxolan-3-ol
• CAS: 129170-69-0
• 化学式: C₆H₁₁IO₂
• 分子量: 242.057
• InChiKey: OAVDFJXSQAZHLN-KVQBGUIXSA-N

物化性质

• 沸点：
  296.0±15.0 °C(Predicted)
• 密度：
  1.771±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+)-(2R,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran 在 三氟甲磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 (-)-(2R,4R,5S)-2-[(Dimethylamino)methyl]-4-benzyloxy-5-methyltetrahydrofuran methiodide
  参考文献：
  名称：

  Synthesis and pharmacological characterization of new chiral derivatives of muscarine and allo-muscarine

  摘要：

  Novel derivatives of natural muscarine and allo-muscarine, i.e. the benzyl ethers (-)-10 and (-)-12 and the benzoate (-)-13, were synthesized in very high enantiomeric excess. Target compounds were tested in vitro on guinea pig tissues, and their muscarinic potency was evaluated at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. The derivatives under study were also assayed in vive on pithed rat. In addition, muscarinic receptor heterogeneity was investigated by determining the affinity and the relative efficacy of compounds (-)-10, (-)-12 and (-)-13 at M-2 (heart force and rate) and M-3 (ileum and bladder) receptor subtypes. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00034-3
• 作为产物：
  描述：

  Methanesulfonic acid 4,4-dimethoxy-5-methyl-tetrahydro-furan-2-ylmethyl ester 在 dipotassium hydrogenphosphate 、 potassium carbonate 、 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 、 水 、 丙酮 为溶剂， 反应 27.5h， 生成 (+)-(2R,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran
  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

文献信息

• Une synthese simple et tres stereoselective de la d, 1-muscarine
  作者：Roger Amouroux、Bernard Gerin、Maurice Chastrette

  DOI：10.1016/s0040-4039(00)85595-1

  日期：1982.1
• DE, AMICI MARCO;DE, MICHELI CARLO;MOLTENI, GIORGIO;PITRE, DAVIDE;CARREA, +, J. ORG. CHEM., 56,(1991) N, C. 67-72
  作者：DE, AMICI MARCO、DE, MICHELI CARLO、MOLTENI, GIORGIO、PITRE, DAVIDE、CARREA, +

  DOI：——

  日期：——