78185-65-6

Usage

Molecular weight

328.34 g/mol

Structure

A pentofuranose sugar molecule with a 1-O-methyl and 2-deoxy substitution, along with two 3,5-di-O-(p-toluoyl) groups attached.

Stereochemistry

The compound has a β-D-erythro configuration.

Potential applications

Synthesis of complex carbohydrates and nucleosides, development of pharmaceutical drugs, and as a chemical probe for studying biological processes.

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 533-67-5 2-Deoxy-D-ribose 
• 76700-79-3 Thiocarbonic acid O-phenyl ester O-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl) ester 
• 67-56-1 methanol 
• 452-51-7 D-2-deoxyribose 

Downstream Products

• 1258432-03-9 1β-(5-bromofuran-2-yl)-1,2-dideoxy-3,5-di-O-p-toluoyl-D-ribofuranose 
• 1258432-04-0 1α-(5-bromofuran-2-yl)-1,2-dideoxy-3,5-di-O-p-toluoyl-D-ribofuranose 
• 441052-40-0 methyl 1-(2'-deoxy-3',5'-di-O-p-toluoyl-α-D-erythropentofuranosyl)-4,5-imidazoledicarboxylate 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 

Relevant academic research and scientific papers

Preparation of pyridine-stretched 2′-deoxyhypoxanthosine phosphoramidite

Pyridine-stretched 2-deoxyhypoxanthosine (strH) phosphoramidite was prepared in eight steps from Hoffer's sugar (2-deoxy-3,5-di-O-(p-toluoyl)-a-D-erythro-pentofuranosyl chloride). Improved synthesis of the Hoffer sugar was achieved without need for distillation or chromatographic separation of intermediates, or use of gaseous HCl. Conditions were optimised to provide a key nitrile intermediate for the preparation of strH whereby the cesium salt of 4(5)-nitroimidazole was glycosylated using Hoffer's sugar. The nitrile intermediate was also used to prepare pyridine-stretched 2-deoxyadenosine (strA) and pyridine-stretched 2-deoxy-2,6-diaminonebulamine (strD). Preliminary studies indicate that strH forms a stronger, size-expanded base pair with adenine compared with the Watson-Crick thymine-adenine base pair.

Template-directed DNA photoligation via α-5-cyanovinyldeoxyuridine

(Chemical Equation Presented) We describe an efficient template-directed photoligation of oligodeoxynucleotides (ODNs) using α-5- cyanovinyldeoxyuridine (αcU). An efficient photoligation was produced by photoirradiation of an ODN containing thymine at the 5′ end with an ODN containing thymine at the 5′ end in the presence of a template ODN. This photoligation method is a new and efficient way to synthesize branched ODNs.

Improved Syntheses of Halofuranose Derivatives with the Desired α-Configuration

Chlorination of ribofuranose or 2-deoxyribofuranose derivatives was carried out in a 1,4-dioxane solution of hydrogen chloride. This improved procedure allowed the syntheses of 1-chloro-α-D-ribofuranose and 1-chloro-2-deoxy-α-D-ribofuranose derivatives and offered ease of handling, high yield, and the stereo-controlled α-configuration at C-1.

NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.

Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.