Novel and Efficient Synthesis of gem-Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)

被引：6

作者：

Pomeisl, Karel ^{[1
]}

Beier, Petr ^{[1
]}

Pohl, Radek ^{[1
]}

Krecmerova, Marcela ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Vvi, Flemingovo Nam 2, Prague 16610 6, Czech Republic

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 10期

关键词：

Difluoromethylation; difluoromethylphosphonate; acyclic nucleoside phosphonate; phosphonate ester; microwave reaction; ASYMMETRIC-SYNTHESIS; FLUORINE; ANALOGS; SUBSTITUTION; INHIBITION; PYRIMIDINE; REAGENT; PURINE;

D O I：

10.1002/slct.201600445

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel efficient method for the synthesis of gem-difluorinated derivatives of acyclic nucleotide analogues has been developed. The method is based on utilization of diethyl difluoromethylphosphonate as a nucleophilic difluoromethylation reagent. In contrast to previous difluoromethylation procedures using commercially available DAST or deoxofluor, this process is very robust, proceeds under mild conditions and is accompanied only by small amounts of by-products. The reaction of diethyl difluoromethylphosphonate with 2-benzyloxyacetaldehyde afforded 3-(benzyloxy)-1,1-difluoropropan-2-ol (6) a key precursor for syntheses of difluoromethylated analogues of various acyclic nucleoside phosphonates.

引用

页码：2102 / 2106

页数：5

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