81703-56-2Relevant academic research and scientific papers
Synthesis of (+)-nojirimycin from 2,3,4,6-tetra-O-benzyl-D-glucopyranose
Moutcl, Stephane,Shipman, Michael
, p. 1403 - 1406 (2007/10/03)
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.
Total Synthesis of (+)-Galactostatin. An Illustration of the Utility of the Thiazole-Aldehyde Synthesis
Dondoni, Alessandro,Perrone, Daniela
, p. 4749 - 4754 (2007/10/02)
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 (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol
Chida,Furuno,Ikemoto,Ogawa
, p. 185 - 194 (2007/10/02)
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.
SYNTHESIS OF (+)-GALACTOSTATIN
Aoyagi, Sakae,Fujimaki, Satoshi,Yamazaki, Naoki,Kibayashi, Chihiro
, p. 783 - 787 (2007/10/02)
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.
Total Synthesis of (+)-Nojirimycin and (+)-1-Deoxynojirimycin
Iida, Hideo,Yamazaki, Naoki,Kibayashi, Chihiro
, p. 3337 - 3342 (2007/10/02)
An efficient chiral synthesis of (+)-nojirimycin (1) and (+)-1-deoxynojirimycin (2) has been achieved in optically pure form via the common intermediate 11 derived from the nonsugar chiral pool.The monosilyl derivative 4 of 2,3-O-isopropylidene-L-threitol (3) was converted to the (E)-allyl alcohol 8, which upon asymmetric epoxidation provided the syn epoxide 9.Regio- and stereoselective epoxide opening reaction of 9 followed by methoxymethylation yielded the azide 11, which afforded in five steps (+)-1-deoxynojirimycin (2).The azide 11 could also serve as the intermediate for the synthesis of (+)-nojirimycin (1), which was thus derived from 11 in six steps.
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.
Legler,Pohl
, p. 119 - 129 (2007/10/02)
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.
