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Synlett 2007(8): 1247-1250
DOI: 10.1055/s-2007-977451
DOI: 10.1055/s-2007-977451
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Facile and General Synthesis of Rare l-Sugar Lactones
Weitere Informationen
Received
16 September 2006
Publikationsdatum:
08. Mai 2007 (online)
Publikationsverlauf
Publikationsdatum:
08. Mai 2007 (online)
Abstract
A facile and general synthesis of rare l-sugar lactones from d-sugars by selectively inverting C-5 was developed. Selective 1-deacylation of sugar perpivaloates by hydroxylamine is described. More practically, β-d-glucose pentaacetate could be transformed to l-idono-1,4-lactones by this simple procedure.
Key words
l-sugar - aldonolactone - 1-deacylation
- 1
Essentials of Glycobiology
Varki A.Cummings R.Esko J.Freeze H.Hart G.Marth J. Cold Spring Harbor; New York: 1999. p.653 -
2a
Gumina G.Chong Y.Choo H.Song G.Chu CK. Curr. Top. Med. Chem. 2002, 2: 1065 -
2b
Wang P.Hong JH.Cooperwood JS.Chu CK. Antivir. Res. 1998, 40: 19 -
2c
Ashley GW. J. Am. Chem. Soc. 1992, 114: 9731 -
2d
Mansuri MM.Farina V.Starrett JE.Benigni DA.Brankovan V.Martin JC. Bioorg. Med. Chem. Lett. 1991, 1: 65 -
3a
Takahashi H.Hitomi Y.Iwai Y.Ikegami S. J. Am. Chem. Soc. 2000, 122: 2995 -
3b
Takahashi H.Iwai Y.Hitomi Y.Ikegami S. Org. Lett. 2002, 4: 2401 - 4
Lee SJ,Seo MJ,Jeong NC,Kim GC,Hong HW, andKim SA. inventors; US 6,448,415. - 5
Acton EM.Ryan KJ.Goodman L. J. Am. Chem. Soc. 1964, 86: 5352 - 6
Haas JW.Kadunce RE. J. Am. Chem. Soc. 1962, 84: 4910 - 7
Hicks A.Fraser-Reid B. Can. J. Chem. 1974, 52: 3367 - 8
Angelotti T.Krisko M.O’Connor T.Serianni AS. J. Am. Chem. Soc. 1987, 109: 4464