2,3,4,6-Tetra-O-acetyl-a-D-glucopyranosyl chloride - CAS 4451-35-8
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1.3-Methoxy-4-(2-nitrovinyl)phenyl glycosides as potential chromogenic substrates for the assay of glycosidases.
Patel A, Richardson AC. Carbohydr Res. 1986 Feb 1;146(2):241-9.
Selective glycosidation of 2,4-dihydroxybenzaldehyde with either 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide, 2-acetamido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride, or 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide afforded the corresponding 4-O-glycosyl derivatives. Subsequent O-methylation, O-deacetylation, and condensation with nitromethane afforded the appropriate beta-glycoside of 3-methoxy-4-(2-nitrovinyl)phenol. The phenol is highly coloured at alkaline pH so that these glycosides may be suitable as chromogenic substrates for the assay of glycosidases.
2.Synthesis and Antimicrobial Screening of Novel Thioglycosides and Acyclonucleoside Analogs Carrying 1,2,3-Triazole and 1,3,4-Oxadiazole Moieties.
Aouad MR1,2. Nucleosides Nucleotides Nucleic Acids. 2016 Jan 2;35(1):1-15. doi: 10.1080/15257770.2015.1109098. Epub 2016 Jan 25.
The solvent-free 1,3-dipolar cycloaddition reaction of dimethylacetylene dicarboxylate (1) with 2-chlorophenyl azide (2) afforded 1,2,3-triazole diester 3 that upon hydrazinolysis, furnished the corresponding bis-acid hydrazide 4. The treatment of compound 4 with carbon disulfide in a refluxing potassium hydroxide solution furnished the desired bis-1,3,4-oxadiazole-2-thione 5 tethered to a 1,2,3-triazole moiety. The respective SOx-glycosides 9-11 were obtained by glycosylation of bis-oxadiazole 5 with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (6), 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide (7), and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride (8) in dry acetone in the presence of Et3N, which acted as a base. However, alkylation of 5 with halogeno-alkanol 12 or 13, chloroglycerol 14, bromoethers 20 or 21, and epichlohydrin 22 in the presence of K2CO3 in DMF yielded the corresponding acyclonucleoside analogs 16-18 and 23-25.
3.Glycosylation of 2-thiohydantoin derivatives. Synthesis of some novel S-alkylated and S-glucosylated hydantoins.
Khodair AI1. Carbohydr Res. 2001 Apr 23;331(4):445-53.
3-Aryl-5-((Z)-arylidene)-3-aryl-2-(2-methylthioethyl)-2-thiohydantoins 3a-f and 3-aryl-5-((Z)-arylidene)-2-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)-2-thiohydantoins 7a-n were prepared from the reaction of 3-aryl-5-((Z)-arylidene)-2-thiohydantoins 2a-n with methylthioethyl chloride or 2',3',4',6'-tetra-O-acetyl-alpha-D-glucopyranosyl bromide via three different routes. The compounds did not display any antiviral and antitumoral activity.
4.Regioselective synthesis, characterization and antimicrobial evaluation of S-glycosides and S,N-diglycosides of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione.
El Ashry el SH1, El Tamany el SH, El Fattah Mel D, Boraei AT, Abd El-Nabi HM. Eur J Med Chem. 2013 Aug;66:106-13. doi: 10.1016/j.ejmech.2013.04.047. Epub 2013 May 20.
Glycosylation of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was investigated in the presence of Et₃N and K₂CO₃ as acid scavengers. A regioselective S-glycosides were obtained by using Et₃N whereas, using K₂CO₃ gave a mixtures of two hybrids having two glycosidic bonds. The two products of each mixture were separated and characterized as S,N(1)- and S,N(2)-bis(glycosylated) derivatives. The structures of the newly synthesized compounds were elucidated by (1)H NMR, (13)C NMR, 2D NMR and mass spectra. The compounds were screened for their antibacterial and antifungal activities. Some compounds exhibited strong inhibition activity compared with the reference drugs (chloramphenicol and baneocin).
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