Synthesis and photoinitiated thiol–ene reactions of exo-mannals – a new route to C-β-D-mannosyl derivatives,RSC Advances

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Synthesis and photoinitiated thiol–ene reactions of exo-mannals – a new route to C-β-D-mannosyl derivatives
RSC Advances ( IF 3.9 ) Pub Date : 2020-9-22 , DOI: 10.1039/d0ra07115c
János József _{1,

2} , Nóra Debreczeni _{2,

3,

4} , Dániel Eszenyi ₃ , Anikó Borbás ₃ , László Juhász ₁ , László Somsák ₁

Affiliation

Syntheses of acyl protected exo-mannal derivatives were developed starting from O-peracylated mannopyranoses via the corresponding anhydro-aldose tosylhydrazones under modified Bamford–Stevens conditions. The synthesis of analogous O-peralkylated (benzylated and isopropylenated) derivatives was carried out from pyranoid and furanoid mannonolactones using methylene transfer reagents. Photoinitiated thiol–ene additions of these exo-mannals resulted in the corresponding C-(mannopyranosyl/mannofuranosyl)methyl sulfides in medium to good yields with exclusive regio- and β(D) stereoselectivities.

中文翻译：

外甘露醛的合成和光引发硫醇-烯反应——C-β-D-甘露糖基衍生物的新途径

在改进的 Bamford-Stevens 条件下，通过相应的脱水醛糖甲苯磺酰腙，从O-过酰化的吡喃甘露糖开始合成酰基保护的外甘露醛衍生物。使用亚甲基转移试剂从吡喃类和呋喃类甘露酸内酯合成类似的O-过烷基化（苄基化和异丙基化）衍生物。这些外甘露醛的光引发硫醇-烯加成产生了相应的C- (吡喃甘露糖基/呋喃呋喃糖基)甲基硫化物，产率中等至良好，具有独特的区域选择性和 β( D ) 立体选择性。

更新日期：2020-09-22

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