64481-90-9

Upstream product

• 14470-28-1 mono-4-methoxytrityl chloride 
• 65-46-3 CYTIDINE 
• 112123-75-8 5'-O-(monomethoxytrityl)-N⁴,2'-O-3'-O-tris<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 
• 148144-72-3 5'-O-(monomethoxytrityl)-N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 
• 88121-72-6 N⁴-<2-(4-nitrophenyl)ethoxycarbonyl>cytidine 

Downstream Products

• 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 
• 197303-74-5 (Z)-Octadec-9-enoic acid (R)-2-{(2-chloro-phenoxy)-[(2R,3R,4S,5R)-5-[2-oxo-4-(4-oxo-pentanoylamino)-2H-pyrimidin-1-yl]-3,4-bis-(4-oxo-pentanoyloxy)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 197303-72-3 Octadecanoic acid (R)-2-{(2-chloro-phenoxy)-[(2R,3R,4S,5R)-5-[2-oxo-4-(4-oxo-pentanoylamino)-2H-pyrimidin-1-yl]-3,4-bis-(4-oxo-pentanoyloxy)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester 
• 197303-70-1 Hexadecanoic acid (R)-2-{(2-chloro-phenoxy)-[(2R,3R,4S,5R)-5-[2-oxo-4-(4-oxo-pentanoylamino)-2H-pyrimidin-1-yl]-3,4-bis-(4-oxo-pentanoyloxy)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester 
• 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 

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.

Nucleosides. Part LI. The 2-(4-Nitrophenyl)ethoxycarbonyl (npeoc) and 2-(2,4-Dinitrophenyl)ethoxycarbonyl (dnpeoc) Groups for Protection of Hydroxy Functions in Ribonucleosides and 2'-Deoxyribonucleosides

The common 2'-deoxypyrimidine and -purine nucleosides, thymidine (4), O4-thymidine (17), 2'-deoxy-N4-cytidine (26), 2'-deoxy-N6-adenosine (39), and 2'-deoxy-N2--O6-guanosine (52) were further protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) and the 2-(2,4-dinitrophenyl)ethoxycarbonyl (dnpeoc) group at the OH functions of the sugar moiety to form new partially and fully blocked intermediates for nucleoside and nucleotide syntheses.The corresponding 5'-O-monomethoxytrityl derivatives 5, 18, 30, 40, and 56 were also used as starting material to synthesize some other intermediates which were not obtained by direct acylations.In the ribonucleoside series, the 5'-O-monomethoxytrityl derivatives 14, 36, 49, and 63 reacted with 2-(4-nitrophenyl)ethyl chloroformate (1) to the corresponding 2',3'-bis-carbonates 15, 37, 50, and 64 which were either detritylated to 16, 38, 51, and 65, respectively, or converted by 1,8-diazabicycloundec-7-ene (DBU) treatment to the 2',3'-cyclic carbonates 66-69.The newly synthesized compounds were characterized by elemental analyses and UV and 1H-NMR spectra.