81703-56-2

Basic information

• Product Name: 5-AMINO-5-DEOXY-GLUCOPYRANOSE BISULFITE
• Synonyms: 5-AMINO-5-DEOXY-GLUCOPYRANOSE BISULFITE;NOJIRIMYCIN BISULFITE;Nojirimycin bisulfite microbial;(2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)-2-piperidinesulfonic acid
• CAS NO: 81703-56-2
• Molecular Formula: C₆H₁₃NO₇S
• Molecular Weight: 243.23
• EINECS: 232-864-1
• Mol File: 81703-56-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /solid
• Storage Temp.: −20°C
• CAS DataBase Reference: 5-AMINO-5-DEOXY-GLUCOPYRANOSE BISULFITE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-5-DEOXY-GLUCOPYRANOSE BISULFITE(81703-56-2)
• EPA Substance Registry System: 5-AMINO-5-DEOXY-GLUCOPYRANOSE BISULFITE(81703-56-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 81703-56-2(Hazardous Substances Data)

Upstream product

• 126441-77-8 5-(tert-butoxycarbonylamino)-5-deoxy-6-O-methoxymethyl-D-glucose dimethyl acetal 
• 108818-03-7 (2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane 
• 108818-09-3 (2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol 
• 108818-08-2 (2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane 
• 109681-01-8 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-β-L-altrofuranose 
• 130193-61-2 (2R,3S,4R,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol 
• 130114-47-5 (2S,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexan-1-ol 
• 130114-46-4 (2S,3S,4S,5R)-5-azido-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol 
• 130114-44-2 (2S,3R,4R,5S)-5-bromo-1-<(tertbutyldimethylsilyl)oxy>-2,3:4,6-bis(isopropylidenedioxy)hexane 
• 130114-43-1 (2S,3R,4S,5S)-2-bromo-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol 
• 130114-45-3 (2S,3R,4R,5S)-5-bromo-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol 
• 130281-95-7 (2S,3S,4S,5R)-5-amino-2,3:4,6-bis(isopropylidenedioxy)hexan-1-ol 
• 168326-10-1 5-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldimethylsilyl)-5-deoxy-2-O,3-O-isopropylidene-5-N,6-O-isopropylidene-D-galactose 
• 109681-00-7 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-α-D-galactofuranose 

Downstream Products

• 14904-83-7 nojirimycin-δ-lactam 
• 15218-38-9 5-amino-5-deoxy-L-altropyranose 
• 15218-38-9 (+)-nojirimycin 
• 15218-38-9 nojirimycin 
• 15218-38-9 nojirimycin 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 107537-94-0 (+)-Galactostatin 
• 107537-94-0 (+)-galactostatin 

Relevant articles and documents

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.

Synthesis of (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol

The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (1a), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural L-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond β-D-glucosidase and bovine liver β-D-galactosidase.

New synthesis of (+)- and (-)-nojirimycin from myo-inositol

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