Related Products of 74808-09-6. Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 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. In a document type is Article, introducing its new discovery.
O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing Benzyl-Protected Glycosyl Donors
The benzyl-protectd glucosyl trichloroacetimidates, phosphates, and halides 1 are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiCl4 in ether, CH2Cl2, CHCl3, or CH3CN and react under these conditions with the model alcohols 3 to give the glycosides 4 in moderate yields.If the alpha-imidate 1a or the beta-phosphate 1d is used as glycosyl donor, in the majority of the cases 1:1 mixtures of the anomers are obtained.In contrast, the beta-imidate 1b gives a distinct excess of the alpha-glycosides and if the alpha-phosphate 1c is employed, the beta-anomers are formed preferentially.Whereas the glycosyl chloride 1f and the glycosyl bromide 1e are not the donors of choice under these conditions, from the beta-fluoride 1g the desired O-glycosides are readily obtained.In 3-5 M solutions of LiClO4 in ether instead of the expected glycosides benzyl protected 1,6-anhydroglucose 6 is formed and the imidazolylcarbonyl-activated carbohydrate 1h reacts with the alcohols 3 to give the glycosyl carbonates 5.Whereas CH2Cl2 and CHCl3 do not influence the stereoselectivity of the glycosylations in ether or CH3CN, the solvent seems to participate in the steric control of the O-glycoside formation. – Keywords: O-Glycoside synthesis; LiClO4 solvent mixtures; Glycosyl phosphates; Glycosyl fluorides; Glycosyl imidates
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics