18006-23-0Relevant academic research and scientific papers
Synthesis of nojirimycin derivatives
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, (2008/06/13)
Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.
Synthesis of nojirimycin derivatives
-
, (2008/06/13)
Nojirimycin δ-lactam and deoxynojirimycin are each synthesized from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-idofuranose as a divergent intermediate by a method which comprises formation of the piperidine ring by connection of nitrogen between C-1 and C-5 with inversion of configuration at C-5 to form nojirimycin δ-lactam or between C-2 and C-6 with inversion of configuration at C-2.
SYNTHESIS OF DEOXYNOJIRIMYCIN AND OF NOJIRIMYCIN δ-LACTAM
Fleet, George W.J.,Carpenter, Neil M.,Petursson, Sigthor,Ramsden, Nigel G.
, p. 409 - 412 (2007/10/02)
The syntheses of nojirimycin δ-lactam and of deoxynojirimycin from a divergent ido-furanose intermediate are reported.
Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue
Broxterman, H. J. G.,Marel, G. A. van der,Neefjes, J. J.,Ploegh, H. L.,Boom, J. H. van
, p. 571 - 576 (2007/10/02)
The easy accessible 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose was converted in six steps into 1,2-O-isopropylidene-3,6-di-O-benzyl-5-deoxy-5-azido-α-D-glucofuranose.The latter afforded, after acidolysis followed by hydrogenolysis, 1-deoxynojirimicine and a small quantity of 1-deoxymannonojirimicine.The antibiotic thus obtained had an inhibitory effect on the trimming of N-linked carbohydrates in IgM.
