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1,6-epithio- and 1,6-episeleno-β-d-glucopyranose: Useful adjuncts in the synthesis of 6-deoxy-β-d-glucopyranosides

✍ Scribed by Robert V Stick; D Matthew; G Tilbrook; Spencer J Williams


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
144 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


The treatment of derivatives of 1,6-epithio-and 1,6-episeleno-/3-D-glucopyranose with various carbohydrate alcohols in the presence of N-iodosuccinimide/triflic acid gives rise to disulfides and diselenides, respectively, which may be transformed to the desired 6-deoxy-fl-D-glucopyranosides.


📜 SIMILAR VOLUMES


Purin-6-yl 6-deoxy-1-thio-β-d-glucopyran
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Pm-in-6-yl 6-deoxy-1-thio-P-o-glucopyranoside ( 4) is a substrate for almond /I-glucosidase and a weak competitive inhibitor of bovine liver P-D-glucuronidase (Ki -20mM). Both 4 and purine-protonated 4 undergo hydrolysis catalyzed by dilute acid in the pH range 0.17-2.59. These results are compared

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Condensation of 2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-cr-D-galactop~anosyl bromide (3) with methyl 2,3,4-tri-O-acetyl-/9-D-galactopyranoside (4) gave a fully acetylated (1+6)-/3-D-galactobiose fluorinated at the 3'-position which was deacetylated to give the title disaccharide. The corresponding trisa