33208-42-3

Upstream product

• 163152-36-1 methyl 5-(tert-butyldiphenylsilyl)-2,3-dibenzoyl-β-D-ribofuranoside 
• 167466-54-8 methyl 5-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranoside 
• 98-88-4 benzoyl chloride 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 163152-35-0 (2R,3S,4R,5R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3,4-diol 
• 148766-45-4 methyl 5-O-trityl-β-D-arabinofuranoside 

Downstream Products

• 782495-97-0 C₂₇H₂₆O₉S 
• 163152-38-3 methyl 1-O-methyl-2,3-dibenzoyl-β-D-ribofuronic acid 
• 163152-39-4 N,1-O-dimethyl-2,3-dibenzoyl-β-D-ribofuranuronamide 
• 163152-37-2 1-O-methyl-2,3-dibenzoyl-β-D-ribofuronic acid 

Relevant academic research and scientific papers

Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals

A nitrogen-centered radical-mediated strategy for preparing 1,2-trans-2-amino-2-deoxyglycosides in one step was established. The cascade amidoglycosylation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO. The benzenesulfonimide radical was electrophilically added to the glycals, and then the resulting glycosidic radical was converted to oxocarbenium upon oxidation by TEMPO+, which enabled the following anomeric specific glycosylation.

Identification of the 5-methylthiopentosyl substituent in Mycobacterium tuberculosis lipoarabinomannan

An unexpected configuration of a novel carbohydrate structure in the cell wall of Mycobacterium tuberculosis was revealed by synthesizing the isomers of 5-deoxy-5-methylthio-D-pentofuranose as α- and β-methyl glycosides, and analyzing their NMR spectra (s

2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors

Adenosine derivatives bearing an N6-(3-iodobenzyl) group, reported to enhance the affinity of adenosine-5'-uronamide analogues as agonists at A3 adenosine receptors (J. Med. Chem. 1994, 37, 636-646), were synthesized starting from methyl β-D-ribofuranoside in 10 steps. Binding affinities at A1 and A(2a) receptors in rat brain membranes and at cloned rat A3 receptors from stably transfected CHO cells were compared. N6-(3- Iodobenzyl)adenosine was 2-fold selective for A3 vs A1 or A(2a) receptors; thus it is the first monosubstituted adenosine analogue having any A3 selectivity. The effects of 2-substitution in combination with modifications at the N6- and 5'-positions were explored. 2-Chloro-N6-(3- iodobenzyl)adenosine had a K(i) value of 1.4 nM and moderate selectivity for A3 receptors. 2-Chloro-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide, which displayed a K(i) value of 0.33 nM, was selective for A3 vs A1 and A(2a) receptors by 2500- and 1400-fold, respectively. It was 46,000-fold selective for A3 receptors vs the Na+-independent adenosine transporter, as indicated in displacement of [3H]N6-(4-nitrobenzyl)-thioinosine binding in rat brain membranes. In a functional assay in CHO cells, it inhibited adenylate cyclase via rat A3 receptors with an IC50 of 67 nM. 2- (Methylthio)-N6-(3-iodobenzyl)-adenosine-5'-N-methyluronamide and 2- (methylamino)-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide were less potent, but nearly as selective for A3 receptors. Thus, 2-substitution (both small and sterically bulky) is well-tolerated at A3 receptors, and its A3 affinity-enhancing effects are additive with effects of uronamides at the 5'- position and a 3-iodobenzyl group at the N6-position.