109784-32-9

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 
• 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 
• 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 
• 130114-48-6 (2R,3S,4S,5R)-2,3:4,6-bis(isopropylidenedioxy)-5-<<<(p-methoxybenzyl)oxy>carbonyl>amino>hexanal 

Downstream Products

• 15218-38-9 5-amino-5-deoxy-L-altropyranose 
• 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.