197303-72-3

Upstream product

• 83200-46-8 2',3',N⁴-trilevulinyl-1-β-D-arabinofuranosylcytosine 
• 194797-00-7 Octadecanoic acid (R)-2-(9H-fluoren-9-ylmethoxycarbonyloxy)-1-octadecanoyloxymethyl-ethyl ester 
• 65-46-3 CYTIDINE 
• 1429-59-0 1,2-distearoyl-sn-glycerol 
• 197303-62-1 4-Oxo-pentanoic acid (2R,3R,4S,5R)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-5-[2-oxo-4-(4-oxo-pentanoylamino)-2H-pyrimidin-1-yl]-4-(4-oxo-pentanoyloxy)-tetrahydro-furan-3-yl ester 
• 57-11-4 stearic acid 
• 64481-90-9 O^5'-(4-methoxy-trityl)-cytidine 
• 87418-74-4 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

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

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.

Synthesis of 1-β-D-arabinofuranosyl-cytosine 5'-phosphate-L-1,2-diacylglycerols

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-ara-cytidine-2',2-anhydro derivative at a 67% yield. 1,2-Dipalmitoyl-sn-glycerol,1,2-distearoyl-sn-glycerol and 1,2-dioleoyl-sn-glycerol were phosphorylated first with 2-chlorphenyl-phosphorobis-triazolide quantitatively. This method was used 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-mesytilensulphonyl chloride (MSCl) and 1-methylimidazole (MeIm) - which was used in the coupling of nucleotides - in an 85-88% yield compared with the low yielding diester method of Ryu et al. Deblocking was carried out in two steps with tetrabutylammonium fluoride (TBAF) and hydrazine hydrate, producing target compounds (9a, 9b, 9c) at a 50% yield.