Oligonucleotidic compounds. XXXII. Phosphorylation of 1-lyxofuranosyl, 1-xylofuranosyl and 1-arabinofuranosyl derivatives of uracil and thymine with triethyl phosphite and hexachloroacetone

A. Holý; F. Šorm

doi:10.1135/cccc19691929

Oligonucleotidic compounds. XXXII. Phosphorylation of 1-lyxofuranosyl, 1-xylofuranosyl and 1-arabinofuranosyl derivatives of uracil and thymine with triethyl phosphite and hexachloroacetone

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19691929 ◽

1969 ◽

Vol 34 (7) ◽

pp. 1929-1953 ◽

Cited By ~ 6

Author(s):

A. Holý ◽

F. Šorm

Keyword(s):

Triethyl Phosphite ◽

Derivatives Of

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Synthesis of N-(2-(2-phosphonylethoxy)ethyl) derivatives of heterocyclic bases

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19900809 ◽

1990 ◽

Vol 55 (3) ◽

pp. 809-818 ◽

Cited By ~ 7

Author(s):

Antonín Holý ◽

Ivan Rosenberg ◽

Hana Dvořáková

Keyword(s):

Triethyl Phosphite ◽

Sodium Salts ◽

Subsequent Hydrolysis ◽

Pyrimidine Bases ◽

Heterocyclic Bases ◽

Derivatives Of

Reaction of bis(2-chloroethyl) ether (II) with triethyl phosphite afforded diethyl 2-chloroethoxyethylphosphonate (III). This compound reacts with sodium salts of heterocyclic bases to give diethyl esters of N-(2-(2-phosphonylethoxy)ethyl) derivatives of purine and pyrimidine bases IV. Compounds IV on reaction with bromotrimethylsilane and subsequent hydrolysis were converted into N-(2-(phosphonylethoxy)ethyl) derivatives IV.

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ChemInform Abstract: PHOSPHORYLATION OF POLYFLUOROAROMATIC COMPOUNDS. II. REACTION OF TRIETHYL PHOSPHITE WITH PENTAFLUORO-SUBSTITUTED DERIVATIVES OF BENZENE

Chemischer Informationsdienst ◽

10.1002/chin.197933276 ◽

1979 ◽

Vol 10 (33) ◽

Author(s):

L. N. MARKOVSKII ◽

G. G. FURIN ◽

YU. G. SHERMOLOVICH ◽

G. G. YAKOBSON

Keyword(s):

Triethyl Phosphite ◽

Derivatives Of

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Synthesis of 2'(3')-phosphates and 2'(3')-phosphorothioates of 5'-O-carboxymethylinosine and related compounds

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19802817 ◽

1980 ◽

Vol 45 (10) ◽

pp. 2817-2829 ◽

Cited By ~ 7

Author(s):

Antonín Holý ◽

Pavol Kois

Keyword(s):

Acid Hydrolysis ◽

Alkaline Hydrolysis ◽

Phosphorus Oxychloride ◽

Triethyl Phosphite ◽

Subsequent Treatment ◽

Disodium Salt ◽

Ethyl Chloroformate ◽

Streptomyces Aureofaciens ◽

Derivatives Of ◽

Related Compounds

5'-O-Carboxymethylinosine (IX) was prepared from disodium salt of 2',3'-O-isopropylideneinosine (VIII) by treatment with sodium chloroacetate, followed by acid hydrolysis. 5'-O-(2-Aminoethylamidocarbonylmethyl)inosine (XIII) was obtained by reaction of IX with p-nitrophenol and subsequent treatment with ethylenediamine. Action of triethyl phosphite on the compounds IX and XIII afforded the corresponding 5'-O-substituted 2'(3')-phosphites X and XIV which on reaction with trimethylsilyl chloride and sulfur gave the 2'(3')-phosphorothioates XI and XV. The compound IX was transformed by phosphorus oxychloride in 5'-O-carboxymethylinosine 2'(3')-phosphate (XII). Uridine, adenosine and inosine 2'(3')-phosphorothioates (Ia-Ic) were obtained from 2',3'-O-di-n-butylstannylene derivatives of the nucleosides IV by treatment with thiophosphoryl chloride followed by alkaline hydrolysis; inosine and guanosine 2'(3')-phosphorothioates (Ic,Id) were prepared by reaction of the corresponding 2'(3')-phosphites VIc, VId with trimethylsilyl chloride and sulfur. Cyclization of Ic and Id with ethyl chloroformate in the presence of tri-n-butylamine afforded inosine 2',3'-O,O-cyclophosphorothioate (VIIc) and the corresponding guanosine derivative VIId. Compounds VIIc and VIId are not cleaved by Streptomyces aureofaciens ribonuclease.

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