(1S,2R,3R)-1-(2-furyl)-2,3-epoxybutan-1-ol | 163277-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutan-1-ol
• 英文别名: (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol；(S)-furan-2-yl-[(2R,3R)-3-methyloxiran-2-yl]methanol
• CAS: 163277-68-7
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: KTTZREMZBSWGHQ-NJUXHZRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutan-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 Celite 、 水 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 pyridinium chlorochromate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 45.67h， 生成 (+)-asperlin
  参考文献：
  名称：

  Enantio- and Diastereoselective Synthesis of (+)-Asperlin by the Sharpless Asymmetric Kinetic Resolution of an Unsymmetrical Divinylcarbinol

  摘要：

  DOI：

  10.3987/com-98-s(h)5
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以63 mg的产率得到(1S,2R,3R)-1-(2-furyl)-2,3-epoxybutan-1-ol
  参考文献：
  名称：

  Total synthesis of (+)-asperlin

  摘要：

  Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.

  DOI：

  10.1016/j.tetasy.2008.04.011

文献信息

• Studies on the sharpless asymmetric epoxidation of unsymmetrical divinylmethanols
  作者：Toshio Honda、Hirotake Mizutani、Kazuo Kanai

  DOI：10.1039/p19960001729

  日期：——

  A reaction of racemic unsymmetrical divinylmethanol rac-13 under the Sharpless asymmetric epoxidation conditions using stoichiometric amounts of titanium tetraisopropoxide [Ti(OPi)4], D-(–)-diisopropyl tartrate (DIPT) and tert-butyl hydroperoxide (TBHP) afforded R-14 and R-15 in 41 and 43% yield, each with > 99%ee, respectively, where the kinetic resolution and subsequent epoxidation had proceeded

  外消旋不对称二乙烯基甲醇rac -13在Sharpless不对称环氧化条件下，使用化学计量的四异丙氧基钛[Ti（OP i）4]，D -（-）-酒石酸二异丙酯（DIPT）和叔丁基氢过氧化物（TBHP）进行反应R -14和R -15的收率分别为41％和43％，ee均> 99％，其中动力学拆分和随后的环氧化反应均以完全区域选择性和非对映选择性的方式进行。
• Peculiar Sharpless kinetic resolution of 2-furylmethanol and its application to the synthesis of (+)-Asperlin
  作者：Zhi-Cai Yang、Wei-Shan Zhou

  DOI：10.1016/0040-4039(95)01170-m

  日期：1995.7

  A peculiar kinetic resolution of E-1-(2-furyl)-2-buten-1-ol (1), which produced two oxidation products, pyranone (2) and epoxyalcohol (3), was developed by using the modified Sharpless reagents. A short synthesis of (+)-Asperlin was achieved starting from the optically active resolution products.

  利用改进的Sharpless试剂，开发了产生两种氧化产物吡喃酮（2）和环氧醇（3）的特殊的E-1-（2-呋喃基）-2-buten-1-ol（1）动力学拆分剂。 。从旋光拆分产物开始，短合成了（+）-Asperlin。
• Concise Enantioselective Synthesis of (+)-Asperlin by Application of the Sharpless Kinetic Resolution to 2-Furylmethanol Derivatives Bearing Alkenyl Moiety on the Side Chain
  作者：Toshio Honda、Nobuko Sano、Kazuo Kanai

  DOI：10.3987/com-94-7001

  日期：——

  A reaction of (+/-)-(E)-1-(2-furyl)but-2-en-1-ol (1) under the Sharpless asymmetric oxidation condition using 30 mol% of D-(-)-diisopropyl tartrate (DIPT), 25 mol% of titanium tetraisopropoxide and 120 mol% of tert-butyl hydroperoxide (TBHP) afforded the (S)-epoxide (3), in 42% yield with high optical purity, which was further converted into an antitumour antibiotic, asperlin (10).
• Yang, Zhi-Cai; Jiang, Xiao-Bin; Wang, Zhi-Min, Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 317 - 321
  作者：Yang, Zhi-Cai、Jiang, Xiao-Bin、Wang, Zhi-Min、Zhou, Wei-Shan

  DOI：——

  日期：——
• Total synthesis of (+)-asperlin
  作者：Hideaki Akaike、Hidekazu Horie、Keisuke Kato、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.04.011

  日期：2008.5

  Syntheses of (+)-asperlin 1 were achieved via two different synthetic routes. 1,2-Addition of alpha-furyl anion to (2R,3S)-2-'butyldimethylsilyloxy-3-chlorobutanal 6 gave (1S,2R,3S)-1-(2-furyl)-2-'butyldimethylsilyloxy-3-chlorobutanol 7, which was converted to the chiral intermediate, (1S,2R,3R)-1-(2-furyl)-2,3-epoxybutanol 8 (37% overall yield from 6) for the synthesis of (+)-1. The second synthesis of (+)-asperlin 1 from (2R,3S)-6 was achieved in 8% overall yield, based on a combination of the indium-assisted stereoselective addition of 3-bromopropenyl acetate 9 to (2R,3S)-6 and the ring closing metathesis (RCM) using Grubbs catalyst. (C) 2008 Elsevier Ltd. All riehts reserved.