Synthetic Route of 14215-68-0. Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide. In a document type is Article, introducing its new discovery.
Synthesis of 1D-(1,3,5/2,4)-4-acetamido-5-amino-1,2,3-cyclohexanetriol and its incorporation into a pseudo-disaccharide
The synthesis of the title compound and 1D-(1,3,5/2,4)-4-acetamido-5-amino-3-O-(beta-D-glucopyranosyluronic acid)-1,2,3-cyclohexanetriol is described.Starting from methyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside 2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzyloxy-5-hydroxycyclohexanone was prepared via a series of transformations including the regioselective ring opening of the benzylidene acetal and the mercury(II)-catalyzed carbocyclic ring closure reaction of 5-en-opyranoside.Stereoselective reduction of ketone 11 with NaBH(OAc)3 gave 1D-(1,2,4/3,5)-2-acetamido-3-O-benzoyl-4-O-benzyl-1,3,4,5-cyclohexanetetrol (88percent), which was then converted into 1D-(1,3,5/2,4)-4-acetamido-5-azido-3-O-benzoyl-2-O-benzyl-1-O-pivaloyl-1,2,3-cyclohexanetriol through selective 5-OH protection, 1-O-mesylation, and subsequent azide displacement.Saponification and hydrogenation of this gave the title compound.Selective O-debenzoylation with 1.1 equiv of K2CO3 in MeOH gave 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-1-O-pivaloyl-1,2,3-cyclohexanetriol (73percent).Glycosylation of this compound with methyl (2,3,4-tri-O-acetyl-alpha-D-glucopyranosyl bromide) uronate in CH2Cl2, using silver triflate as the promoter, afforded 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol (20) in 79percent yield.Finally, O-deacylation and subsequent hydrogenation of this compound gave the basic pseudo-disaccharide.Keywords: Glycosidase inhibitor; Pseudo-aminosugar; Ferrier’s carbocylization
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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics