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DOI: 10.1055/s-2008-1067226
A Synthesis of 1-Lithiated Glycals and 1-Tributylstannyl Glycals from 1-Phenylsulfinyl Glycals via Sulfoxide-Lithium Ligand Exchange
Publication History
Publication Date:
13 August 2008 (online)
Abstract
1-Lithiated glycals generated by reaction of 1-phenylsulfinyl glycals with either t-BuLi or PhLi are transformed to 1-tributylstannyl glycals on reaction with tributyltin chloride.
Keywords
lithium - tin - sulfoxides - carbohydrates - glycals
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0001th:
- Primary Data (added August 26th, 2009). FIDs and associated files for the 1H, 13C and DEPT NMR spectra for compounds 14, (S S)-23, (S S)-25, (R S)-26, 27, (S S)-28, (R S,S S)-29, 30, (R S)-36, (S S)-36, (S S)-37, 38, (R S)-39, (S S)-39, (S S)-44, (R S)-46, (S S)-46, (R S)-48, (S S)-48, (S S)-49, 52, (R S)-53, (R S)-55, (R S)-57, (S S)-57, (S S)-58, (R S)-61, (S S)-61, (R S)-62, (S S)-62, (R S)-65 and (S S)-65 are summarized.
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References
The Bu3SnMgBr was prepared by transmetallation of Bu3SnLi with MgBr2. The Bu3SnLi was prepared, in turn, by the reaction of BuLi with Bu3SnSnBu3 thereby generating 1 equiv of Bu4Sn waste for each equiv of Bu3SnLi.
30Parker and Su (reference 26) reported a successful metallation of the bis-TBS-protected analogue of 35 using 3 equiv of t-BuLi in THF at -78 ˚C.
40Crystallographic data for the structures in this paper have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 685328 [( S S )-44], 676297 [(R S)-36], 676296 [(R S)-48], 676300 [(R S)-55], 676298 [(S S)-28], 676301 [(S S)-61], 682926 [(S S)-37]. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/retrieving.html.