A new route to aminosugars from sugar nitrones: synthesis of 6-deoxynojirimycin

(1S)-(Z)-2-Benzyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamineN-oxide

“…There are three bonds originating from the N atom: one to an O atom, another to a Csp 2 and a last one to a Csp 3 atom. In our case, these distances are 1.303 (2), 1.278 (2) and 1.486 (2) A Ê , respectively, compared to respective values in other structures of 1.309, 1.288 and 1.490 A Ê (Huber et al, 1985), 1.308, 1.302 and 1.492 A Ê (Baskaran et al, 1998), and 1.289, 1.288 and 1.496 A Ê (Dhavale et al, 1997). If we consider the H atom set on the Csp 3 atom, we can de®ne a dihedral angle between the two planes de®ned by Csp 2 /N/Csp 3 and N/Csp 3 /H.…”

“…8.67 (Huber et al, 1985), 3.26 (Baskaran et al, 1998) and 6.43 (Dhavale et al, 1997). Thus, there is a correlation between the dihedral angle value and the Csp 2 ÐN length, i.e.…”

“…nitrones bearing a stereogenic center contiguous to the N atom (Huber et al, 1985;Baskaran et al, 1998;Dhavale et al, 1997). Such nitrones are of interest as potential precursors for the stereoselective synthesis of amine derivatives.…”

Chiron approaches to polyhydroxylated piperidines: promising glycosidase inhibitors

“…In this method, we have visualized the formation of piperidine ring skeleton in 3 by joining C-N bond between C-5 amino-and C-1 aldehyde functionality of D-glucose derivative. The C-5 amino sugar was therefore an apparent key intermediate that could be obtained from 1,3-addition of methylmagnesium bromide to D-glucose derived nitrone 6 . Thus, the reaction of 1,2-Oisopropylidene-3-O-benzyl-α-D-xylo-pentodialdose (4) with N-benzylhydroxylamine hydrochloride, in the presence of sodium acetate in methanol-water, afforded a nitrone 5 (Scheme 1).…”

C‐Glycosides, Array‐based Addressable Libraries, and the Versatility of Constant Current Electrochemistry

“…C‐mannoside derivatives, such as 2 , were developed as metabolically stable alternatives to O‐mannosides resulting in lead compounds with a longer half‐life and higher oral bioavailability in animal studies. Similar approaches to biological problems have led to a family of useful aryl C‐glycoside derivatives . Hence, a solution developed in the context of the FimH‐related C‐glycosides has the potential to be generally useful and also applied to other systems and saccharides.…”