J. E. Marugg

A convenient and general approach to the synthesis of properly protected d-nucleoside-3′-hydrogenphosphonates via phosphite intermediates

Abstract Evidence will be presented to show that the monofunctional phosphitylating reagents bis(N,N-di-ethylamino)chlorophosphine and salicylchlorophosphine are very effective for the preparation of 5′-0,N-protected d-nucleoside-3′-hydrogenphosphonates.

A new and versatile approach to the preparation of valuable deoxynucleoside 3′-phosphite intermediates

Abstract The easily accessible and crystalline monofunctional phosphitylating reagent bis-(diisopropylamino) chlorophosphine has been used for the synthesis of phosphoramidites and H-phosphonates of d-nucleosides and, also, the formation of 3′-5′-internucleotidic phosphonate bonds.

An approach to the synthesis of α-l-fucopyranosyl phosphoric mono- and diesters via phosphite intermediates

Abstract The reagent chloro-β-cyanoethyl-N,N-diisopropylamino-phosphoramidite reacts smoothly with the anomeric hydroxyl group of a properly protected (benzyl) α-L-fucopyranose to afford a relatively stable phosphite intermediate in high yield. The latter can easily be converted into valuable α-L-fucopyranosyl phosphoric mono- and diesters.

A Convenient and General Approach to the Synthesis of Properly Protected d-Nucleoside-3′-hydrogenphosphonates via Phosphite Intermediates.

Aus den Nucleosiden (I) entstehen mit dem Salicyl-chlorphosphit (II) die Substitutionsprodukte (III), die mit Pyridin/ Wasser zu den Phosphonaten (IV) reagieren.

Side Products in Nucleotide Chemistry

Abstract Alkyl bisaminophosphorodiamidites1 (1) has been shown to be versatile reagents for in situ preparation of d-nucleoside-3-phosphoramidites2,3,4 (2.)

Polymer Supported Synthesis of Deoxyoligonucleotides using In Situ Prepared Deoxynucleoside 2-Cyanoethyl Phosphoramidites

Abstract 2-Cyanoethyl bis(diisopropylamino) phosphorodiamidite (1) is a stable and easily obtainable compound1 which, when activated with 0.5 eq. tetrazole, gives solutions of deoxyribonucleoside 2-cyano-ethyl phosphoramidites (2) useful for the synthesis of deoxyoligo-nucleotides. 2 Our results applying these in-situ prepared phosphoramidites for polymer-supported syntheses of a variety of deoxyoligonucleotides (DNA fragments) will be presented.