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Publications [#328801] of Vasant Kaiwar

Papers Published

  1. Kaiwar, V; Reese, CB; Gray, EJ; Neidle, S, Synthesis of 9- [cis-3-(Hydroxymethyl)cyclobutyl]-adenine and -guanine, Journal of the Chemical Society, Perkin Transactions 1 no. 18 (January, 1995), pp. 2281-2287, Royal Society of Chemistry (RSC) [doi]
    (last updated on 2021/01/22)

    Abstract:
    2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to ally1 benzyl ether 14, was converted in four steps and in ˜40% overall yield into trans-3-(benzyloxymethy1)cyclobutanol llb. The latter alcohol l l b was coupled under Mitsunobu conditions with 6- (4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21b to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3- (hydroxymethyl)cyclobutyl]guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported. © 1995 by the Royal Society of Chemistry. All Rights Reserved.


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