GB621094A - A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom - Google Patents

A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom

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Publication number
GB621094A
GB621094A GB336647A GB336647A GB621094A GB 621094 A GB621094 A GB 621094A GB 336647 A GB336647 A GB 336647A GB 336647 A GB336647 A GB 336647A GB 621094 A GB621094 A GB 621094A
Authority
GB
United Kingdom
Prior art keywords
adenosine
orthophosphate
diaralkyl
pyrophosphate
give
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB336647A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to GB336647A priority Critical patent/GB621094A/en
Publication of GB621094A publication Critical patent/GB621094A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Abstract

Adenosine - 51 - diaralkyl - orthophosphates in which the hydroxyl groups in the 21- and 31-positions of the b -furanoso side chain are protected, e.g. by two acyl groups or by a dialkyl methylidene group, are prepared by treating adenosine, in which the said hydroxyl groups are protected, with a diaralkyl halogenophosphonate in the presence of a tertiary base. Hydrolysis of the product gives adenosine-51-aralkyl-orthophosphate which is hydrogenolysed to adenosine - 5 - orthophosphate. The hydrolysis and hydrogenolysis steps may take place in the reverse order. By treating the metal salt of adenosine-51-aralkyl-orthophosphate, such as the silver salt, with a diaralkyl halogenophosphonate and subsequently removing the diaralkyl groups by hydrogenolysis, adenosine-51-pyrophosphate is obtained. The preferred starting material is 21 : 31-iso-propylidene-adenosine, but 21 : 31-diacetyl-adenosine may also be used. In examples: (1) 21 : 31-isopropylideneadenosine in pyridine is treated with dibenzyl chlorophosphonate to give 21 : 31-isopropylideneadenosine-51-dibenzyl-orthophosphate which is hydrogenated with a palladium oxide catalyst and hydrolysed to give adenosine-51-orthophosphate and (2) 21 : 31-isopropylidene adenosine-51-dibenzyl-orthophosphate prepared as in (1) is hydrolysed to adenosine-51-benzylorthophosphate which is converted to the silver salt and treated with dibenzylchlorophosphonate to give a tribenzyl pyrophosphate which is in turn hydrogenolysed to adenosine-51-pyrophosphate. Adenosine-51-pyrophosphate forms an acridine salt.
GB336647A 1947-02-05 1947-02-05 A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom Expired GB621094A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB336647A GB621094A (en) 1947-02-05 1947-02-05 A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB336647A GB621094A (en) 1947-02-05 1947-02-05 A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom

Publications (1)

Publication Number Publication Date
GB621094A true GB621094A (en) 1949-04-04

Family

ID=9756962

Family Applications (1)

Application Number Title Priority Date Filing Date
GB336647A Expired GB621094A (en) 1947-02-05 1947-02-05 A process for the manufacture of adenosine-5-diaralkyl-phosphate derivatives and adenosine-5-phosphate and 5-pyrophosphate derived therefrom

Country Status (1)

Country Link
GB (1) GB621094A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3201388A (en) * 1962-04-20 1965-08-17 Ajinomoto Kk Method of preparing 5'-ribonucleotides
US3288780A (en) * 1962-01-30 1966-11-29 Ajinomoto Kk Process for preparing 5'-ribonucleotides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288780A (en) * 1962-01-30 1966-11-29 Ajinomoto Kk Process for preparing 5'-ribonucleotides
US3201388A (en) * 1962-04-20 1965-08-17 Ajinomoto Kk Method of preparing 5'-ribonucleotides

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