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Synthesis 2021; 53(03): 509-517
DOI: 10.1055/s-0040-1706569
DOI: 10.1055/s-0040-1706569
feature
Synthesis of Pyridiniumboranephosphonate Diesters and Related Compounds using Trityl Cation as a Borane Hydride Acceptor
Financial support from the National Science Centre, Poland (Narodowe Centrum Nauki, Preludium Grant Nr 2018/31/N/STP/03589 to J.G.), is greatly acknowledged.
Abstract
Boranephosphonate diesters react with pyridine and some tertiary amines in the presence of dimethoxytrityl chloride used as a borane hydride acceptor, to afford the boron-modified phosphodiester analogues containing a P-B-N structural motif. The reaction provides a convenient entry to pyridinium- and ammoniumboranephosphonates derived from the corresponding alkyl, aryl, or nucleoside boranephosphonate diesters. Some aspects of the synthetic protocol, mechanistic features related to a possible intermediate involved, and the role of the solvents used, are discussed.
Key words
H-phosphonates - boranephosphonates - pyridiniumboranephosphonates - trityl cation - nucleotide analoguesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706569.
- Supporting Information
Publication History
Received: 01 September 2020
Accepted after revision: 06 October 2020
Article published online:
09 November 2020
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14 Within 15 min, the signal at δP = 59 ppm disappeared and was replaced with a broad resonance at ca. δP = 72 ppm (δB = –21 ppm), tentatively assigned to the corresponding chloroboranephosphonate (MS analysis). This was accompanied by a gradual conversion of diethyl H-phosphonate into its P-dimethoxytritylated derivative (signal at ca. δP = 27 ppm).
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15 At this stage of the investigations, no attempt was made to maximize the isolated yields of compounds 3 and 4.
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