87418-74-4

Basic information

• Product Name: 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one
• Synonyms: 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one
• CAS NO: 87418-74-4
• Molecular Weight: 515.566
• Mol File: 87418-74-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one(87418-74-4)
• EPA Substance Registry System: 4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one(87418-74-4)

Safety Data

• Hazardous Substances Data: 87418-74-4(Hazardous Substances Data)

Upstream product

• 14470-28-1 mono-4-methoxytrityl chloride 
• 147-94-4 arabinosyl cytosine 
• 64481-90-9 O^5'-(4-methoxy-trityl)-cytidine 
• 65-46-3 CYTIDINE 

Downstream Products

• 87418-75-5 N⁴-benzoyl-5'-O-monomethoxytritylarabinocytidine 
• 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 
• 160186-52-7 N⁴-benzoyl-5'-O-monomethoxytritylarabinocytidine-3'-O-N,N-diiso-propyl-β-cyanoethylphosphoramidite 
• 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 
• 87418-81-3 4-Amino-1-{(2R,3S,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 
• 87418-80-2 4-Amino-1-{(2R,3S,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 

Relevant articles and documents

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.

Hybridization properties of oligoarabinonucleotides

3'-Phosphoramidite derivatives of arabinocytidine, arabinoadenosine, and arabinouridine were prepared and used for the solid-phase synthesis of oligoarabinonucleotides (arabinonucleic acid, or ANA). Thermal denaturation analysis and gel mobility shift ass