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EP0131993A2
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Phosphorylating agent; a process for the preparation thereof; a process for phosphorylating an organic hydroxyl or amine compound
Assignee: Radboud Universiteit Nijmegen
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Filing: 1984-06-29
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Granted: —
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Expires: 2004-06-29
Abstract
Abstract The invention relates to phosphorylating agents containing at least one protected hydroxyl group and at least one leaving group. According to the invention, a methylsulphonylethyl group (Mse) is used as the hydroxyl protecting group. Typical examples of such phosphorylating agents are the compounds (MseO) 2 POL, (MseO) POLL', (MseO) 2 PL and (M-seO)PLL', in which L and L' are leaving groups. The invention also relates to processes for preparing these phosphorylating agents and processes for the phosphorylation of organic hydroxyl or amine compounds, in particular nucleosides and (poly)nucleotides.
Inventors
- 👤 Godefridus Ignatius Tesser
- 👤 Christianus Adrianus Arnoldus Claesen
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-28 21:20
CPC Classifications
C; C07; C07H; C07H11/00; C07H11/04; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091; C07F9/094; C07F9/12; C07F9/14; C07F9/141; C07F9/146; C07F9/547; C07F9/6527; C07F9/6533; C07F9/6564; C07F9/6571; C07F9/6574; C07F9/65744; C07H19/00; C07H19/02; C07H19/04; C07H19/16; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
29 words
A phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized in that it contains at least one hydroxyl group protected by methyl-sulphonylethyl.
Claim 2
Dependent Claim
29 words
A phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized in that it contains at least one hydroxyl group protected by methyl-sulphonylethyl.
Claim 3
Dependent Claim
40 words
A phosphorylating agent according to claim 1, characterized in that it satisfies any of the formulae 1-4, in which Mse represents the methylsulphonylethyl group CH 3 SO 2 CH 2 CH 2 -, and L and L' represent leaving groups.
Claim 4
Dependent Claim
22 words
A phosphorylating agent according to claim 2, characterized in that L and/or L' represent chlorine; 1,2,4 triazolyl; tetrazolyl; phthalimidooxy; succinimidooxy or benzotriazolooxy.
Claim 5
Dependent Claim
17 words
A phosphorylating agent according to claim 3, characterized in that it satisfies formula 5 or formula 6.
Claim 6
Dependent Claim
49 words
A process for preparing a phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized by preparing, in a manner known for analogous compounds, a phosphorylating agent containing at least one hydroxyl group protected by methylsulphonylethyl, as defined in any of claims 1-4.
Claim 7
Dependent Claim
44 words
A process for preparing a phosphorylating agent containing at least one protected hydroxyl group and at lea one leaving group, characterized by preparing a compound having formula 5 by reacting 2-methylsulphonylethyl alcohol in an inert solvent successively with PCl 3 and C1 2 .
Claim 8
Dependent Claim
44 words
A process for preparing a phosphorylating agent containing at least one protected hydroxyl group and at lea one leaving group, characterized by preparing a compound having formula 5 by reacting 2-methylsulphonylethyl alcohol in an inert solvent successively with PCl 3 and C1 2 .
Claim 9
Dependent Claim
15 words
A process according to claim 6, characterized in that said inert solvent is dry tetrahydrofuran.
Claim 10
Dependent Claim
35 words
A process according to claim 6 or 7, characterized in that the reaction with PCl 3 is carried out at a temperature of 0-10°C, and the reaction with Cl 2 at a temperature of 15-30°C.
Claim 11
Dependent Claim
70 words
A process for preparing a phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized by preparing a compound having formula 6 by refluxing 2-methylsulphonylethyl alcohol, with exclusion of water, in an excess of PC1 3 with stirring until no more HCl escapes any longer, whereafter distilling of the excess of PC1 3 , and distilling the remaining oily liquid at a reduced pressure.
Claim 12
Dependent Claim
70 words
A process for preparing a phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized by preparing a compound having formula 6 by refluxing 2-methylsulphonylethyl alcohol, with exclusion of water, in an excess of PC1 3 with stirring until no more HCl escapes any longer, whereafter distilling of the excess of PC1 3 , and distilling the remaining oily liquid at a reduced pressure.
Claim 13
Dependent Claim
27 words
A process according to claim 9, characterized in that the 2-methyl-sulphonylethyl alcohol isrefluxed in a fourfold to eightfold excess of PC1 3 at a temperature of 90-100°C.
Claim 14
Dependent Claim
32 words
A process according to claim 9 or 10, characterized in that the oily liquid remaining after distilling off the excess of PCl 3 is distilled at a reduced pressure in a Kugelrohr.
Claim 15
Dependent Claim
53 words
A process for phosphorylating an organic hydroxyl or amine compound by reacting the same with a phosphorylating agent containing at least one protected hydroxyl group and at least one leaving group, characterized by using a phosphorylating agent containing at least one hydroxyl group protected by methylsulphonylethyl, as defined in any of claims 1-4.
Claim 16
Dependent Claim
40 words
A process according to claim 12, characterized by phosphorylating a nucleoside derivative, nucleotide derivative, or polynucleotide derivative containing a free 3 1- hydroxyl group or a free 5'-hydroxyl group, and in which the other reactive groups, if present, are protected.
Claim 17
Dependent Claim
28 words
A process according to claim 12 or 13, characterized in that the product of phosphorylation, if it is a phosphite triester, is oxidized to form a phosphate triester.
References Cited (Backward Citations)
No citation records indexed.
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