109784-33-0

Usage

Uses

Used in Pharmaceutical Applications:
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid is used as a pharmaceutical agent for its potential biological activity, leveraging its complex structure and functional groups to interact with biomolecules and exhibit specific chemical and biological properties.
Used in Chemical Synthesis:
In the chemical industry, (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid is used as a building block or intermediate in the synthesis of more complex molecules, taking advantage of its reactive functional groups for further chemical modifications.
Used in Material Science:
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidine-2-sulfonic acid is utilized in material science for the development of new materials with unique properties, such as hydrogels or polymers, due to its ability to form hydrogen bonds and interact with other molecules.

Upstream product

• 109681-01-8 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-β-L-altrofuranose 
• 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 
• 109681-00-7 5-amino-5-deoxy-1,2-O-isoproylidene-6-O-trityl-α-D-galactofuranose 
• 130114-48-6 (2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal 
• 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 
• 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 

Downstream Products

• 15218-38-9 5-amino-5-deoxy-L-altropyranose 
• 108147-55-3 D-galactono-δ-lactam 
• 107537-94-0 (+)-Galactostatin 
• 107537-94-0 (+)-galactostatin 

Relevant academic research and scientific papers

Total Synthesis of (+)-Galactostatin. An Illustration of the Utility of the Thiazole-Aldehyde Synthesis

The natural aza sugar (+)-galactostatin (+)-1 has been prepared from D-serine by sequential installation of chiral 1C and 2C units employing thiazole-based reagents.Thus, the D-serine-derived methyl ester 3 was transformed by 2-thiazolyllithium (4) into t

SYNTHESIS OF (+)-GALACTOSTATIN

The chiral synthesis of (+)-galactostatin (3), a new β-galactosidase inhibitor, has been achieved, in which the key step involved a diastereoselective epoxidation of the allylic alcohol (4) derived from L-tartaric acid.

Synthesis of 5-amino-5-deoxy-D-galactopyranose and 1,5-dideoxy-1,5-imino-D-galactitol, and their inhibition of alpha- and beta-D-galactosidases.

A 12-step route is presented starting from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose for the preparation of the title compounds and their L-altro analogues. Their synthesis is based on the reduction with Raney nickel of a protected 5-hydroxyimino derivative of L-arabino-hexofuranos-5-ulose, with the following improvements for the preparation of a D-galactofuranose derivative: oxidation at C-3 with pyridinium dichromate-acetic anhydride, stereospecific reduction of a 3-O-acetyl-hex-3-enofuranose intermediate to the D-gulo derivative, and inversion at C-3 of its 3-tosylate with tetrabutylammonium acetate in chlorobenzene. alpha-D-Galactosidase from coffee beans and from Escherichia coli and beta-D-galactosidase from E. coli and Aspergillus wentii were inhibited with Ki values that ranged from 0.0007 to 8.2 microM. Formation of the enzyme-inhibitor complexes with the D-galactose analogue was on the time-scale of minutes, whereas the D-galactitol analogue showed a slow approach to the inhibition only with alpha-D-galactosidase from coffee beans and beta-D-galactosidase from A. wentii. N-Alkylation of the D-galactitol analogue was detrimental to the inhibition except for beta-D-galactosidase from E. coli and beta-D-glucosidase from almonds, but, even with these enzymes, the observed affinity enhancements were 10(2) to 10(3)-times smaller than those of N-alkylated D-galactosylamine and D-glucosylamine.