An improved synthesis of 1-β-D-arabinofuranosylcytosine 5'-phosphate- L-1,2-diacylglycerols

Article abstract of DOI:10.1080/07328319808004734

5'-O-MMTr-cytosine arabinoside was prepared on a large scale from 5'-O- MMTr-cytidine with diphenyl carbonate via 5'-protected cytidine - 2',3'- carbonate - aracytidine-2',2-anhydro derivative at a 67 % yield. The synthesis of 1,2-L-dipalmitoyl-sn-glycerol, 1,2-L-distearoyl-sn-glycerol and 1,2-L-dioleoyl-sn-glycerol described here using 9-fluorenylmethoxycarbonyl (FMOC) group for protection of 3-position of glycerol which can be selectively removed by Et₃N treatment on the overall 60-70 % yield based on 1,2,-isopropilidene-sn-glycerol. These glycerols were phosphorylated first with 2-chlorophenyl-phosphoro-bis-triazolide quantitatively in order to avoid acyl migration, then the glycerophosphate intermediates were condensed with 2',3',N⁴-trileulinyl-1-β-D-arabinofuranosylcytosine in the presence of 2- mesytilenesulphonyl chloride (MsCl) and 1-methylimidazole (MeIm)- which was used in the coupling of nucleotides- in an 85-95 % yield compared with the low yielding diester method of Ryu. Deblocking was carded out in two steps with tetrabutylammonium fluoride (TBAF) and hydrazine hydrate, producing target compounds (14a, 14b, 14c) at a 50 % yield.

Full text of DOI:10.1080/07328319808004734

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An Improved Synthesis of 1-β-D-
Arabinofuranosylcytosine 5′-Phosphate-
L-1,2-diacylglycerols
Ágnes Nyilas a
a Department of Bioorganic Chemistry , Biomedical Center, Uppsala
University , S-751 23, Uppsala, Sweden
Published online: 22 Aug 2006.
To cite this article: Ágnes Nyilas (1998) An Improved Synthesis of 1-β-D-Arabinofuranosylcytosine
5′-Phosphate-L-1,2-diacylglycerols, Nucleosides and Nucleotides, 17:9-11, 1953-1967, DOI:
10.1080/07328319808004734
To link to this article: http://dx.doi.org/10.1080/07328319808004734
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