155006-24-9

Upstream product

• 68045-07-8 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose 

Downstream Products

• 172740-32-8 C₂₇H₂₆N₂O₈S 
• 113886-72-9 1-(2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone 

Relevant academic research and scientific papers

Pyrimidine nucleoside compounds and oligonucleoside compounds containing same

Novel 2- and 4-substituted pyrimidine nucleosides and oligonucleosides are provided, as are methods and intermediates useful in preparing same. In preferred embodiments, one of the 2- and 4-substituents is =O, =NH, or =NH2+ and the other is Q, =C (RA)-Q,

Apparatus and processes for the large scale generation and transfer of diazomethane

For large scale preparation of pyrimidine ribonucleosides, the intermediate 2-O-methyl-(or ethyl)-1,3,5-tri-O-benzoyl-α-D-ribose can be prepared using a diazomethane (or diazoethane) reaction that is controlled via an inert solvent transferring system. This transfer system allows for large scale preparations of the pyrimidine ribonucleosides.

Synthesis of novel C-2 substituted pyrimidine nucleoside analogs

A series of 2-(2-oxoalkylidene)-4(1H)-pyrimidinone nucleoside analogs were synthesized by the addition of the lithium enolates of methylketones to 2,5'- and 2,2'-anhydrouridines and to 2,5'-anhydrothymidines. Alternatively, 2- thiouridine was alkylated with bromomethyl ketones to yield 2-(2- oxoalkyl)thio-4(1H)-pyrimidinone ribofuranosides in good yields. These intermediates were subsequently transformed into the title compounds via an Eschenmoser sulfur extrusion reaction. The 2-(2-oxoalkylidene)-4-(1H)- pyrimidinone nucleoside analogs exhibit enol proton signals in their 1H nmr spectra indicative of hydrogen bonding between N-3 and keto oxygen. These structures offer functional groups with potential for Watson-Crick hydrogen bonding.