230636-22-3

Upstream product

• 230636-19-8 (3S,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-one 
• 53929-48-9 (2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol 
• 230636-21-2 (3S,4R,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-dimethoxyhexan-2-one 

Downstream Products

• 230636-24-5 2,3,4,6-Tetra-O-benzyl-5-[N-(tert-butoxycarbonyl)amino]-5-deoxy-D-glucose dimethyl acetal 
• 230636-30-3 (2R,3S,4R)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5,5-dimethoxy-pentylamine 

Relevant academic research and scientific papers

An efficient synthesis of aldohexose-derived piperidine nitrones: Precursors of piperidine iminosugars

D-Glucopyranose-derived and L-idopyranose-derived piperidine nitrones were synthesized in good overall yields through six-step reaction sequence starting from readily available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The method is efficient and could be general for the synthesis of aldohexose-derived piperidine nitrones which are precursors of piperidine iminosugars.

Synthesis of (+)-nojirimycin from 2,3,4,6-tetra-O-benzyl-D-glucopyranose

Synthesis of the antibiotic (+)-nojirimycin has been accomplished starting from commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose 2. This D-glucopyranose derivative was converted into the D-glucopyranose dimethyl acetal 5 by thioacetalisation, C-5 oxidation and transacetalisation with methanol. Introduction of the 5-amino substituent with the correct D-g/i/co-stereochemistry was realised by conversion of ketone 5 into the corresponding oxime 6, followed by diastereoselective reduction with lithium aluminium hydride. After protection of the resulting primary amine as its tert-buly] carbamate, the desired D-g/i/co-amine 7 could be separated from the unwanted L-;Y/o-isomer 8. Hydrogenolysis of 7 followed by treatment with aqueous sulfur dioxide yielded 1-deoxynojirimycin-l-sulfonic acid 9, which was further transformed into (+)-nojirimycin 1.