79816-14-1Relevant academic research and scientific papers
Apparatus and processes for the large scale generation and transfer of diazomethane
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, (2008/06/13)
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.
General preparative synthesis of 2'-O-methylpyrimidine ribonucleosides
Ross,Springer,Vasquez,Andrews,Cook,Acevedo
, p. 765 - 769 (2007/10/02)
A convergent and general approach to synthesizing 2'-O-methylpyrimidine ribonucleosides 4a-e-, 6, 7 on a multigram scale is described which begins with an improved procedure for making larger quantities of 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose. The sugar was reacted with the desired silylated pyrimidines at room temperature under Vorbruggen conditions. The crude products contained less than 10% of the α anomers and the desired β anomers were isolated by crystallization. The blocked nucleosides were then deprotected and isolated by standard methods.
Synthesis of 2',3'-Differentiated Ribonucleosides via Glycosylation. Reactions with 2-O-Me or 2-O-TBDMS Ribofuranose Derivatives. 1. Pyrimidine Series
Chavis, C.,Dumont, F.,Wightman, R. H.,Ziegler, J. C.,Imbach, J. L.
, p. 202 - 206 (2007/10/02)
The synthesis of 2',3' asymmetrically substituted pyrimidine ribonucleosides in 70-95percent yields by using modified Vorbruggen conditions with "nonparticipating" 2-O-CH3 and 2-O-TBDMS ribofuranoses is described.Such compounds are useful synthons for oligoribonucleotide synthesis, including incorporation of "rare" bases.New and practically useful conditions for placement (using 1,2,4-triazole) and removal (KF/crown ether) of the tert-butyldimethylsilyl (TBDMS) protecting group are also reported.
