(1S,2R)-3-Benzyloxy-1-furan-2-yl-propane-1,2-diol | 180682-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-3-Benzyloxy-1-furan-2-yl-propane-1,2-diol
• CAS: 180682-00-2
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: PQHYLNYXULVLPE-OCCSQVGLSA-N

物化性质

• 沸点：
  428.680±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.234±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (1S,2R)-3-Benzyloxy-1-furan-2-yl-propane-1,2-diol 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-((R)-2-Benzyloxy-1-hydroxy-ethyl)-6-hydroxy-6H-pyran-3-one
  参考文献：
  名称：

  An expedient preparation of chiral building blocks having levoglucosenone chromophore: a new enanticontrolled route to (–)-β-multistriatin and (+)-exo-brevicomin

  摘要：

  2-Alkenylfurans are transformed enantioselectively into the bicyclic enones having the levoglucosenone chromophore, whose synthetic utility is demonstrated by a stereocontrolled synthesis of two insect pheromones (-)-beta-multistriatin and (+)-exo-brevicomin.

  DOI：

  10.1039/cc9960001477
• 作为产物：
  描述：

  Benzyl (E)-3-(2-furyl)prop-2-enyl ether 在 甲基磺酰胺 、 AD-mix-β 、 水 作用下， 以 叔丁醇 为溶剂， 反应 12.0h， 以72%的产率得到(1S,2R)-3-Benzyloxy-1-furan-2-yl-propane-1,2-diol
  参考文献：
  名称：

  An expedient preparation of chiral building blocks having levoglucosenone chromophore: a new enanticontrolled route to (–)-β-multistriatin and (+)-exo-brevicomin

  摘要：

  2-Alkenylfurans are transformed enantioselectively into the bicyclic enones having the levoglucosenone chromophore, whose synthetic utility is demonstrated by a stereocontrolled synthesis of two insect pheromones (-)-beta-multistriatin and (+)-exo-brevicomin.

  DOI：

  10.1039/cc9960001477

文献信息

• <i>De Novo</i> Asymmetric Synthesis of a 6-<i>O</i>-Methyl-<scp>d</scp>-<i>glycero</i>-<scp>l</scp>-<i>gluco</i>-heptopyranose-Derived Thioglycoside for the Preparation of <i>Campylobacter jejuni</i> NCTC11168 Capsular Polysaccharide Fragments
  作者：Roger A. Ashmus、Anushka B. Jayasuriya、Ying-Jie Lim、George A. O’Doherty、Todd L. Lowary

  DOI：10.1021/acs.joc.6b00296

  日期：2016.4.1

  An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-d-glycero-l-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably, compared to the only previous synthesis of this molecule, this approach significantly reduces the number

  对映体选择性从头6-的硫代糖苷衍生物的合成ö甲基d -甘油基-升-葡糖-heptopyranose残余物在所找到的空肠弯曲杆菌荚膜多糖报道：NCTC11168（2 HS）。该化合物从糠醛衍生的手性二醇以11个步骤获得。值得注意的是，与该分子仅有的先前合成方法相比，该方法显着减少了获得靶标所需的纯化步骤。