Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines

Abstract

Stereoselective synthesis of N-alkyl-D-allosamines, designed for the preparation of N-alkyl derivatives of allosamidin (a chitinase inhibitor), is achieved by a 'carbonyl group transfer' reaction followed by stereoselective reduction and this method represents the first example of N-alkyl-D-allosamines synthesized from a 2-oxosugar.

A T‐Shaped Nickel(I) Metalloradical Species

“…For the ligand synthesis, 4,5‐dibromo‐2,7,9,9‐tetramethyl‐9,10‐dihydroacridine was prepared following the literature procedures . The two pendant phosphine arms were installed by lithiation and subsequent phosphination with P i Pr 2 Cl.…”

Syntheses of Orthogonally Protected d‐Galactosamine, d‐Allosamine and d‐Gulosamine Thioglycoside Building Blocks with N‐phthalimido Groups

“…The inversion at C3 of a N ‐acetylglucosamine has also been reported by the Mitsunobu type inversion using triphenylphosphine, benzoic acid and diethyl azodicarboxylate (DEAD) . So far as the strategy of the inversion via the triflate is concerned, it has been applied to a 1,6‐anhydroglucosamine for the C3−OH inversion towards the synthesis of an allosamine derivative . The inversion of the C3−OH via the triflate has also been reported for a azidoglucose derivatives .…”

A Facile and Efficient One‐Pot Synthesis of Substituted Quinolines from α‐Arylamino Ketones Under Vilsmeier Conditions

“…The efficiency of the cyclization proved to be suitable for α-arylamino ketones 1b-m, which afforded the corresponding substituted quinolines 2b-m in good yields (Table 2, entries 2-13). The versatility of the quinoline synthesis was evaluated by performing the reaction with 1-aryl-2-(naphthalen-1-ylamino)ethanones 1n-p (Table 2, entries [14][15][16]. When 2-(m-toluidino)-1-phenylethanone (1q) was subjected to identical conditions, the reaction furnished a product that was characterized as 7-methyl-3-phenylquinoline (2q; Table 2, entry 17).…”

“…In our recent work we have demonstrated the utility of the Vilsmeier reagent in the synthesis of functionalized heterocycles, such as substituted 2H-pyrans, [15] pyridines, [16] 1H-pyrazoles [17] and pyridin-2(1H)-ones. [18] Thus, as a continuation of previous work and following on our research interest in the synthesis of highly valuable heterocycles, we have prepared a series of α-arylamino ketones and examined their reactivity towards different Vilsmeier reagents.…”