Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

Abstract

A concise and convenient route that may be easily scaled is reported for the preparation of unprotected beta-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding beta-D-glucopyranosides in good to high yields. Primary alcohols gave only beta-D-glucopyranosides. A mechanism is proposed for this transformation. [reaction: see text]

Synthesis ofN-acetyl Glucosamine Analogs as Inhibitors for Hyaluronan Biosynthesis

“…Compound 8 was conveniently prepared in large quantities from commercially available GlcNAc 7 using anhydrous FeCl 3 as a catalyst in acetone. [31] With oxazoline 8 in hand, methylation of its free 3-OH group by MeI and NaH gave compound 9 in quantitative yield. Subsequent acid-catalyzed hydrolysis of compound 9 with p -toluene sulfonic acid (PTSA) furnished the desired 3- O -methyl- N -acetyl- d -glucosamine 1 , which was acetylated using acetic anhydride in pyridine to give the product 4 in 50% overall yield over the two steps (Sch.…”

Muramyl Dipeptide and its Derivatives: Peptide Adjuvant in Immunological Disorders and Cancer Therapy

“…On the other hand, 2-methyl-(1,2-dideoxy-5,6- O -isopropylidene-α-D-glucofurano-[2, 1-d])-2-oxazolin 3 (Scheme 4) is accessible from 2-acetamido-2-deoxy-D-glucose in one step on a large scale 88 . The oxazoline moiety already contains the NAc group of MurNAc in a masked form.…”

A facile method for steroid labeling by heavy isotopes of hydrogen

“…Hz, J¼9.9 Hz, 2-CH) 13. C NMR (75 MHz, CDCl 3 ) d:10.09 (28-CH 3 ),11.93 (18-CH3 ), 12.88 (21-CH 3 ), 13.12 (19-CH 3 ), 16.21 (26-CH 3 ), 21.34 (4-CH 2 ), 21.36 (27-CH 3 ), 22.00 (11-CH 2 ), 24.07 (15-CH 2 ), 27.40, 27.59 (25-CH), 27.80 (16-CH 2 ), 27.94 (C(CH 3 ) 2 ), 37.67 (20-CH), 38.23 (8-CH), 39.12 (1-CH 2 ), 39.54 (12-CH 2 ), 41.60 (13-C), 42.92 (10-C), 44.01 (24-CH), 46.89 (7-CH 2 ), 50.71 (5-CH), 53.00 (9-CH), 53.54 (17-CH), 56.41 (14-CH), 74.23 (2-CH), 80.57 (23-CH), 82.53 (22-CH), 108.26 (C(CH 3 ) 2 ), 154.87 (OC(O) 2 ), 209.84 (6-CO), (3-CD) missing.…”