Synthesis and Biological Activity of Isopolar Acyclic Nucleotide Analogs

Holý, Antonı́n

doi:10.1016/b978-044450951-2/50007-2

Cited by 10 publications

(17 citation statements)

References 288 publications

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“…Evaporation of solvents gave a crude product which was chromatographed on a silica gel column in hexanes : EtOAc = 4 : 1 to 2 : 1 to afford phosphonate 11 as an oil (61.6 g, 70%). 1 …”

Section: General Methodsmentioning

confidence: 99%

“…After drying (Na 2 SO 4 ) the solvents were evaporated to give a crude product which was chromatographed on silica gel in hexanes : EtOAc = 3 : 1 to 0 : 100 and then CH 2 Cl 2 : MeOH = 10 : 1) leaving oxirane 12 (58.5 g, 91%) as an oil. 1 …”

Section: Diisopropyl (E)-2-(oxiranyl)ethylphosphonate (12)mentioning

confidence: 99%

“…Evaporation of the solvent afforded the crude product which was chromatographed on silica gel in CH 2 Cl 2 : MeOH = 100 : 1 to 50 : 1 to 30 : 1 providing compound 8 (48.0 g, 83%). 1 …”

Section: Diisopropyl (E)-2-hydroxymethyl-1-cyclopropylphosphonate (8)mentioning

confidence: 99%

“…Combined organic phase was dried (Na 2 SO 4 ), the solvent was evaporated and the residue was chromatographed on a silica gel column in hexanes : EtOAc : MeOH = 30 : 60 : 1 to EtOAc : MeOH = 5 : 1 leaving compound 15 (60 g, 76% in three steps) as an oil. 1 …”

Section: Diisopropyl (E)-2-(phenylselenenylmethyl)-1-cyclopropylphospmentioning

confidence: 99%

“…The solvent was evaporated to give crude product 13 (170 g) containing Ph 3 PO (ratio 1 : 2.7, estimated yield of 13 was 88%) which was employed in the next step. 1 A solution of (PhSe) 2 (34.9 g, 0.112 mol) in EtOH (350 mL) was refluxed till all selenide was dissolved (30 min). After cooling to rt, 4M NaOH (56 mL, 0.225 mol) was added followed by NaBH 4 (7.67 g, 0.225 mol).…”

Section: Diisopropyl (E)-2-(phenylselenenylmethyl)-1-cyclopropylphospmentioning

confidence: 99%

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Synthesis of methylenecyclopropane analogues of antiviral nucleoside phosphonates

et al. 2006

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Synthesis of methylenecyclopropane analogues of nucleoside phosphonates 6a, 6b, 7a and 7b is described. Cyclopropyl phosphonate 8 was transformed in four steps to methylenecyclopropane phosphonate 16. The latter intermediate was converted in seven steps to the key Z-and Emethylenecyclopropane alcohols 23 and 24 separated by chromatography. Selenoxide eliminations (15 → 16 and 22 → 23 + 24) were instrumental in the synthesis. The Z-and E-isomers 23 and 24 were transformed to bromides 25a and 25b which were used for alkylation of adenine and 2-amino-6-chloropurine to give intermediates 26a, 26b, 26c and 26d. Acid hydrolysis provided the adenine and guanine analogues 6a, 6b, 7a and 7b. Phosphonates 6b and 7b are potent inhibitors of replication of Epstein-Barr virus (EBV).

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“…Evaporation of solvents gave a crude product which was chromatographed on a silica gel column in hexanes : EtOAc = 4 : 1 to 2 : 1 to afford phosphonate 11 as an oil (61.6 g, 70%). 1 …”

Section: General Methodsmentioning

confidence: 99%

Section: Diisopropyl (E)-2-(oxiranyl)ethylphosphonate (12)mentioning

confidence: 99%

“…Evaporation of the solvent afforded the crude product which was chromatographed on silica gel in CH 2 Cl 2 : MeOH = 100 : 1 to 50 : 1 to 30 : 1 providing compound 8 (48.0 g, 83%). 1 …”

Section: Diisopropyl (E)-2-hydroxymethyl-1-cyclopropylphosphonate (8)mentioning

confidence: 99%

Section: Diisopropyl (E)-2-(phenylselenenylmethyl)-1-cyclopropylphospmentioning

confidence: 99%

Section: Diisopropyl (E)-2-(phenylselenenylmethyl)-1-cyclopropylphospmentioning

confidence: 99%

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