216976-56-6

Upstream product

• 114861-16-4 Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 87-72-9 D-Xylose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 23345-80-4 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 2504-55-4 3'-amino-3'-deoxyadenosine 
• 58699-62-0 3'-Azido-3'-deoxyadenosine 
• 216976-57-7 3-azido-3-deoxy-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 216976-62-4 3-azido-5-O-(4-phenylbenzyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 216976-71-5 Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-72-6 Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 659722-26-6 C₃₅H₃₅N₃O₆Si 

Relevant academic research and scientific papers

DERIVATIVES OF MONOSACCHARIDES FOR DRUG DISCOVERY

New compounds and methods for the preparation of combinatorial libraries of potentially biologically active compounds are based on monosaccharides of formula (I) being a derivative of a furanose or pyranose form of a monosaccharide.

Synthesis of 3'-azido- and 3'-amino-3'-deoxyadenosine in both enantiomeric forms

Aminosugar nucleosides are important bioactive molecules of which puromycin, a derivative of 3'-amino-3'-deoxyadenosine, is one of the most important examples. Some azidosugar nucleosides, the synthetic precursors of the corresponding aminosugar compounds, are known to be active against HIV reverse transcriptase. We are interested in comparing the bioactivity of D- and L-enantiomers of such nucleosides. Here, the synthesis of both D- and L- enantiomers of 3'-azido- and 3'-amino-3'-deoxyadeonsine, respectively, is described. It begins with the introduction of the nitrogen functionality through a substitution reaction with inversion at C-3 of a D- or L-xylose derivative, respectively. The azidosugar is converted into an appropriate glycosyl donor which is the submitted to a glycosidation reaction according to Vorbruggen. Deprotection affords 3'azido-3'-deoxy-D/L-adenosine, our potentially antiviral target compounds, and reduction of the azido substituent leads to the aminosugar target molecules.

Glycosamino acids: New building blocks for combinatorial synthesis

In order to produce inexpensive, chemically diverse carbohydrate building blocks more amenable for use in combinatorial organic synthesis, amine and carboxylic acid functional groups were incorporated into several monosaccharides. A series of 12 new glycosamino acids was prepared from commercially available starting materials. Conventional peptide synthesis solution coupling techniques were used to ligate glycosamino acids, producing oligomeric 'glycotides'. Finally, a library of glycotides was produced by coupling of a glycosamino acid mixture to a rigid template.