40632-45-9

Upstream product

• 951-78-0 2'-deoxyuridine 
• 93-97-0 benzoic acid anhydride 
• 4104-89-6 triphenylpropargyl stannane 
• 62232-29-5 3',5'-di-O-benzoyl-2'-bromo-2'-deoxyuridine 
• 24850-33-7 allyltributylstanane 
• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 175024-33-6 C₂₃H₂₉N₂O₇P 
• 31616-01-0 3’,5’-O-benzoyl-2,2’-anhydrouridine 
• 613-90-1 benzoyl cyanide 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 145828-13-3 α-D-1,3,5-tri-O-benzoyl-2-O-[3-(trifluoromethyl)benzoyl]ribofuranose 
• 98-88-4 benzoyl chloride 
• 31501-22-1 N⁴-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine 

Downstream Products

• 1161403-57-1 3',5'-di-O-benzoyl-2'-deoxy-5-methylselenyluridine 
• 77180-96-2 C₂₃H₁₉FN₂O₇ 
• 2968-28-7 α-2'-deoxy-5-fluorouridine 
• 135080-78-3 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyl)-1H-pyrimidine-2,4-dione 
• 123606-62-2 5'-O-Benzoyl-2'-desoxy-β-D-ribofuranosyluracil 
• 135080-77-2 C₃₁H₂₈N₂O₈ 
• 139954-93-1 C₂₆H₂₁F₃N₂O₇ 

Relevant academic research and scientific papers

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.

Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.

Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters

(Chemical Equation Presented) N,O-Peracylated cytidine and 2′-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125°C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

5-(E)-Bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use

The present invention relates to pyrimidine nucleoside compounds and their use to treat viral infections of Varicella Zoster virus and Epstein Barr Virus, as well as cancers which are complications of Epstein Barr virus.

Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides

The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.

Synthesis of 2'-α-C-allenyl-2'-deoxyuridine: An analogue of 2'-azido- 2'-deoxyuridine, known inhibitor of ribonucleotide diphosphate reductase (RDPR)

The 1,2-propadienyl (allenyl) group was introduced by means of a radical reaction at the 2'-α- C position of uridine to prepare the rifle compound as a novel analogue of 2'-azido-2'-deoxyuridine, a known inhibitor of RDPR.

A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates

A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.