Synthetic Route of 14215-68-0, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide, molecular formula is C8H15NO6. In a Article，once mentioned of 14215-68-0
Benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (5) was synthesized by the treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (3) with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl bromide in the presence of silver trifluoromethanesulfonate and s-collidine.O-Deacetylation, followed by oxidation with acetic anhydride-dimethyl sulfoxide, and stereoselective reduction with sodium borohydride, converted 5 into benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-beta-D-mannopyranosyl)-alpha-D-glucopyranoside (8).Catalytic hydrogenation of 8 gave 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucopyranose, which was converted into 2-methyl-<3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-mannopyranosyl)-alpha-D-glucopyrano>–<2,1-d>-2-oxazoline (13), by treatment with hydrogen chloride-acetyl chloride, followed by chloride-ion catalysis.Condensation of 13 with 3 gave the trisaccharide, benzyl O-(2,3,4,6-tetra-O-acetyl-beta-D-mannopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (14).Removal of the O-acetyl and O-benzyl groups from 14 gave the title compound.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics