(2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol | 102735-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol
• 英文别名: 2,5-anhydro-1-iodo-1,3,6-trideoxy-L-xylo-hexitol；(2S,3S,5S)-5-(iodomethyl)-2-methyloxolan-3-ol
• CAS: 102735-38-6
• 化学式: C₆H₁₁IO₂
• 分子量: 242.057
• InChiKey: OAVDFJXSQAZHLN-ZLUOBGJFSA-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)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(2S,5S)-5-methyl-2-(iodomethyl)-4(2H)-dihydrofuranone
  参考文献：
  名称：

  穆斯卡隆和异丁烯酮的对映异构体的合成及药理研究。

  摘要：

  基于使用（R）-和（S）-乳酸酯作为起始原料的策略，可以合成穆斯卡隆[（-）-1和（+）-1]和别甲香酮[（-）- 5和（+）-5]的对映体过量大于98％。检查了化合物与大脑皮层（M1），心脏（M2）和唾液腺（M3）的膜结合以及识别毒蕈碱受体亲和激动剂状态的能力。还通过五种功能测定法测试了两对对映异构体，并确定了它们的毒蕈碱效力。在结合力和功能测试中，（-）-1（2S，5S）和（-）-5（2R，5S）分别是穆斯卡隆和异源香豆素的体。在功能测试中评估的穆斯卡隆的普遍比例在280-440之间。这些值与（2.4-10。1）文献报道。从立体化学的观点来看，穆斯卡隆的行为与穆斯卡因和所有其他主要的毒蕈碱激动剂相同。结果，解释穆斯卡隆异常的假说不再存在。

  DOI：

  10.1021/jm00088a029
• 作为产物：
  描述：

  Benzoic acid (2S,3S,5S)-5-formyl-2-methyl-tetrahydro-furan-3-yl ester 在 咪唑 、 sodium tetrahydroborate 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 6.5h， 生成 (2S,4S,5S)-2-Iodomethyl-5-methyl-tetrahydrofuran-4-ol
  参考文献：
  名称：

  由d-葡萄糖发散合成（+）- Muscarine和（+）- Epi -Muscarine

  摘要：

  通过利用d-葡萄糖作为手性前体，实现了（+）-毒蕈碱和（+）-表-毒蕈碱的立体定向合成。合成的关键步骤包括将3,5-二-O-磺酰基-d-呋喃呋喃糖衍生物进行立体定向环化成相应的2,5-酸酐，以及2,5-脱水-1-苏-hex-2的立体定向氢化。-烯化乙缩醛衍生物，从而提供了以完全立体有择的方式制备两个目标分子的不同中间体的途径。

  DOI：

  10.1016/s0040-4020(00)00482-8

文献信息

• A concise synthesis of (+)-muscarine
  作者：T. H. Chan、C. J. Li

  DOI：10.1139/v92-346

  日期：1992.11.1

  (+)-Muscarine was synthesized from S-(−)-ethyl lactate in five steps with the application of a zinc-mediated allylation reaction in aqueous media. Reversal of chelation-control stereoselectivity wa...

  (+)-毒蕈碱是在水介质中应用锌介导的烯丙基化反应，从乳酸 S-(-)-乙酯分五步合成的。螯合控制立体选择性的逆转...
• Synthesis of (2R,3S)-1,2,3-Butanetriol Derivatives From (R)-2,3-O-Isopropylideneglyceraldehyde and of the (2S,3R)-Enantiomers FromD-Glucose. Application to the Synthesis of Enantiomerically Pure Muscarine
  作者：Johann Mulzer、Alfred Angermann、Winfried Münch、Günter Schlichthörl、Angelo Hentzschel

  DOI：10.1002/jlac.198719870103

  日期：1987.1.31

  Both enantiomers of the O-protected epoxy alcohol derivative 1b have been prepared from (R)-2,3-O-isopropylideneglyceraldehyde and D-glucose, respectively, and utilized in a practical synthesis of L- and D-muscarine iodide and chloride.

  O-保护的环氧醇衍生物1b的两种对映体分别由（R）-2，3 - O-异亚丙基甘油醛和D-葡萄糖制备，并用于L-和D-穆斯卡因碘化物和氯化物的实际合成中。
• Synthesis and pharmacological characterization of new chiral derivatives of muscarine and allo-muscarine
  作者：Marco De Amici*、Clelia Dallanoce、Piero Angeli*、Gabriella Marucci、Franco Cantalamessa、Carlo De Micheli

  DOI：10.1016/s0014-827x(00)00034-3

  日期：2000.8

  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.
• Chemoenzymic synthesis of the eight stereoisomeric muscarines
  作者：Marco De Amici、Carlo De Micheli、Giorgio Molteni、Davide Pitre、Giacomo Carrea、Sergio Riva、Sandro Spezia、Lucia Zetta

  DOI：10.1021/jo00001a015

  日期：1991.1

  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.
• 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：——