13-Sep-2021 News Discovery of (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

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Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, causing turnover rates to depend strongly on interfacial structure and composition. 74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate, molecular formula is C36H36Cl3NO6. In a Article,once mentioned of 74808-09-6, Electric Literature of 74808-09-6

2-Hydroxy-4,6-dimethoxyacetophenone (4) was glycosylated with O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl) trichloroacetimidate (5) and trimethylsilyl triflate as promoter to yield directly the C-glycoside 6.Construction of the flavone system by application of a Baker-Venkataraman-type rearrangement followed by deprotection yielded isoembigenin (2).Glycosylation of 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone (17) with the trichloroacetimidate 5 afforded the O-glycoside intermediate 18 which was converted via Fries rearrangement into the C-glycoside 21.Applying again the Baker-Venkataraman rearrangement and cyclization gave isovitexin and vitexin derivatives 25 and 26, which were completely deprotected to yield isovitexin (1b) and vitexin (1a), respectively. – Key Words: Glycosides / Flavones / Vitexin / Isovitexin / Isoembigenin / Carbohydrates / Trichloroacetimidates / Fries rearrangement / Baker-Venkataraman rearrangement

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics