Awesome Chemistry Experiments For (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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In an article, published in an article, once mentioned the application of 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, is a conventional compound. this article was the specific content is as follows.HPLC of Formula: C36H36Cl3NO6

O-Glycosyl Imidates, 29. – Reaction of O-(Glucopyranosyl)Imidates with Electron-Rich Heterocycles. – Synthesis of C-Glucosides

The O-benzyl-protected alpha-glucosyl trichloroacetimidate 1 gives with furan and derivatives and ZnCl2-OEt2 as catalyst via 2-C attack the alpha-C-glucosides 2-alpha – 4-alpha.Good results in this reaction are also obtained with the aryl-substituted glucosyl imidate 5 as glycosyl donor.The alpha-configurations in the products assigned through 1H-NMR data were secured by the reaction of the 2-O-acyl-O-glucosyl trichloroacetimidate 14 with 2-methylfuran. 2′-O-Benzylation of the product provides the C-glucoside 3-beta with beta-configuration, the anomer of compound 3-alpha.The C-glucosylfurans synthesized give with acetylenedicarboxylate cycloadducts, they undergo electrophilic substitution at the 5-position, and they are directly C-lithiated with lithium diisopropylamide.The corresponding C-glucosylation of thiophene and 2-methylthiophene with the trichloroacetimidate 1 provide the alpha-C-glucosides 15-alpha and 16-alpha whereas 1,2-dimethylindole lead to the corresponding beta-C-glucoside 18-beta.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics