The Chemistry and Structure of Thep(o)nc(o) System. Part 2. Crystal Andmolecular Structure of N-Diethoxyphosphorylformamidine

CycloSal‐nucleosyl‐phosphate triesters are a known class of highly effective nucleotide prodrugs (pronucleotides) of antivirally active nucleoside analogues. Until recently, the synthesis of these compounds always gave diastereoisomeric mixtures. Then, a convergent route for the stereospecific synthesis of cycloSal‐triesters was described to give isomerically pure cycloSal‐prodrugs for the treatment of viral diseases. Here, the development of a stereoselective synthesis of these pronucleotides using various chiral auxiliaries is described. In contrast to pyrrolidine‐ or pyrrolidinone derivatives it was found that a thiazolidine derived from valinol fulfilled all three requirements to act as a suitable chiral moiety, allowing: (i) strong chirality transfer, (ii) the formation of separable diastereoisomeric intermediates, and (iii) a suitable leaving group that allows the introduction of the nucleoside analogue (e.g., d4T) in the final step under mild reaction conditions. The title compounds were obtained with very high diastereoisomeric excesses of more than 95 %.

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Linear Synthesis of Chiral cycloSal‐Pronucleotides

Morales

Román

Thomann

et al. 2011

Eur J Org Chem

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The chemistry and structure of the P(O)NC(O) system. Part 3. Preparation of O,O‐diethyl‐N‐acylphosphoramidates and their reactions with electrophiles

Bauermeister

Modro

Zwierzak

1993

Heteroatom Chemistry

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Six 0, O-diethyl-N-acylphosphorarnidates (la-f) were synthesized. The reactions of their conjugate bases with haloalkanes were studied. The N/(phosphoryl)O/(carbonyl)O regioselectivity varied greatly, depending on the substrate, the haloalkane, the base, and other reaction conditions. The earlier [I71 reaction of N-formyl substrate la that led to the Nphosphorylated fomzamidine was extended to other substrates 1. Again, the yields and the selectivity depended strongly on the structure of a substrate.

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THE CHEMISTRY AND STRUCTURE OF THE P(O)NC(O) SYSTEM. PART 1. TRIMETHYLSILYLATION OF O,O-DIETHYL-N-FORMYLPHOSPHORAMIDATE AND THE HEXAMETHYLDISILAZANE-PROMOTED CONVERSION TO THEN-PHOSPHORYLATED FORMAMIDINE

Bauermeister

Modro

1992

Phosphorus, Sulfur, and Silicon and the Related Elements

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The Chemistry and Structure of Thep(o)nc(o) System. Part 2. Crystal Andmolecular Structure of N-Diethoxyphosphorylformamidine

Cited by 4 publications

References 8 publications

Linear Synthesis of Chiral cycloSal‐Pronucleotides

Linear Synthesis of Chiral cycloSal‐Pronucleotides

The chemistry and structure of the P(O)NC(O) system. Part 3. Preparation of O,O‐diethyl‐N‐acylphosphoramidates and their reactions with electrophiles

THE CHEMISTRY AND STRUCTURE OF THE P(O)NC(O) SYSTEM. PART 1. TRIMETHYLSILYLATION OF O,O-DIETHYL-N-FORMYLPHOSPHORAMIDATE AND THE HEXAMETHYLDISILAZANE-PROMOTED CONVERSION TO THEN-PHOSPHORYLATED FORMAMIDINE

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