📜1,2:5,6-Di-O-Isopropylidene-3-O-Trifluoromethanesulfonyl-α-D-Allofuranose置于cesium Fluoride体系中,用 1,4-二氧六环,水,叔丁醇 用作溶剂,化学反应 44.0H,反应生成3-氟-3-脱氧-D-吡喃糖
参考文献:3-Fluoroazetidinecarboxylic Acids And Trans,Trans-3,4-Difluoroproline As Peptide Scaffolds: Inhibition Of Pancreatic Cancer Cell Growth By A Fluoroazetidine Iminosugar
标题:3-Fluoroazetidinecarboxylic Acids And Trans,Trans-3,4-Difluoroproline As Peptide Scaffolds: Inhibition Of Pancreatic Cancer Cell Growth By A Fluoroazetidine Iminosugar
摘要:Reverse Aldol Opening Tenders Amides Of 3-Hydroxyazetidinecarboxylic Acids (3-Oh-Aze) Unstable Above Ph 8. Axe,Found In Sugar Beet,Is Mis-Incorporated For Proline In Peptides In Humans And Is Associated With Multiple Sclerosis And Teratogenesis. Axe-Containing Peptides May Be Oxygenated By Prolyl Hydroxylases Resulting In Potential Damage Of The Protein By A Reverse Aldol Of The Hydroxyazetidine; This,Rather Than Changes In Conformation; May Account For The Deleterious Effects Of Axe. This Paper Describes The Synthesis Of 3-Fluoro-Aze Amino Acids As Hydroxy-Aze Analogues Which Are Not Susceptible To Aldol Cleavage. 4-(Azidomethyl)-3-Fluoro-Aze And 3,4-Difluoroproline Are New Peptide Building Blocks. Trans,Trans-2,4-Dihydroxy-3-Fluoroazetidine,An Iminosugar,Inhibits The Growth Of Pancreatic Cancer Cells To A Similar Degree As Gemcitabine.
Doi:10.1021/acs.Joc.5B00463