A general strategy for the stereoselective synthesis of l-1-deoxyallonojirimycin and d-1-deoxygulonojirimycin

Synthesis, conformational study, glycosidase inhibitory activity and molecular docking studies of dihydroxylated 4- and 5-amino-iminosugars

“…57 Selective deprotection of 5,6-acetonide functionality with 1% H 2 SO 4 afforded diol 12 in 88% yield. 58 Diol 12 on treatment with sodium metaperiodate in acetoneewater followed by reduction with sodium borohydride in methanolewater afforded a primary alcohol 13 in 87% yield (two steps). 59 The primary hydroxyl group of 13 was converted to a tosyl derivative 14 (TsCl, Py) 59 and then to a C-5 azido compound 15 (NaN 3 , DMF) in 87% yield.…”

Synthesis and Glycosidase Inhibition Study of 2‐C‐Hydroxymethyl‐ and 6‐C‐Hydroxymethyl‐Branched Piperidines from D‐Glucose Using Ene‐Yne Metathesis as a Key Step

“…Compound 8 could then be easily synthesized from D ‐glucose. Thus, the synthesis proceeded from olefin 10 (see Scheme ), which was obtained from D ‐glucose in six steps by following literature procedures 14,15. The N ‐propargylation of compound 10 was achieved by treatment with NaH and propargyl bromide in N , N ‐dimethylformamide (DMF) at 0 °C to afford the desired product 8 in 93 % yield.…”

C‐Branched Imino Sugars: Synthesis and Biological Relevance

“…Vankar and co‐workers reported an innovative route starting from the readily available 1,2:5,6‐di‐ O ‐isopropylidene‐α‐glucofuranose 106 (Scheme ) , . Based on a previous report by Ghosh and co‐workers, they synthesized the 1,3‐diene 109 by mean of an ene‐yne metathesis.…”