2002
DOI: 10.1021/ja027850u
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First and Efficient Synthesis of Phosphonodifluoromethylene Analogues of Nucleoside 3‘-Phosphates:  Crucial Role Played by Sulfur in Construction of the Target Molecules

Abstract: Phosphoric esters of secondary alcohols are ubiquitous in biological systems. However, despite the obvious interest of the corresponding difluoromethylene phosphonates as isopolar mimics, a single example of such an analogue featuring this particular substitution pattern has so far been reported in the literature, due to synthetic problems associated with their preparation. The lithium salt of diethyl difluoromethylphosphonothioate 28d provides a solution to this problem, as demonstrated by an 8-step synthesis… Show more

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Cited by 33 publications
(34 citation statements)
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“…Thus, sequentially treating 40a-c with 6 Eq. of trimethylsilylbromide at 80 8C for 1 h, and water delivered phosphonic acid 41a-c, which were converted to the final nucleotide analogues 42 by the action of ammonia in methanol; the target molecules were conveniently isolated as sodium salts by standard purification with Dowex 50X-2 resin [27][28][29].…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Thus, sequentially treating 40a-c with 6 Eq. of trimethylsilylbromide at 80 8C for 1 h, and water delivered phosphonic acid 41a-c, which were converted to the final nucleotide analogues 42 by the action of ammonia in methanol; the target molecules were conveniently isolated as sodium salts by standard purification with Dowex 50X-2 resin [27][28][29].…”
Section: Resultsmentioning
confidence: 99%
“…However, all attempts to react this substrate with phosphonyl or phosphonothioyl radicals failed to deliver the expected adducts 25 or 52, respectively, the starting material being recovered in each case (Scheme 12) [27].…”
Section: Resultsmentioning
confidence: 99%
“…98 Carbocyclic dinucleoside polyphosphonates have shown activity against HIV reverse transcriptase-catalyzed DNA synthesis and hence demonstrate antiviral activity. 59, 101 60, 102 61, 103 62,104 and 63, 105 Fig. 99 It is important to note here that synthetic access to biologically interesting cyclic and acyclic a-uorophosphonate and a,a-diuorophosphonate nucleoside(-tide) analogs has been well studied and reviewed (e.g.…”
Section: A-bromophosphonocarboxylates and Abromobisphosphonatesmentioning
confidence: 99%
“…A synthesis of 3′‐deoxyribofuranose nucleoside analogues 31–33 (Fig. ) bearing the α,α ‐(difluoromethylene)phosphonate group at the position 3 of the tetrahydrofurane ring was developed with an attempt to prepare new potential antivirals, but no data were published . Later, a synthesis of the compound 34 (Fig.…”
Section: Cyclic Nucleoside Phosphonatesmentioning
confidence: 99%