These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: A novel synthesis of 2-deoxy-alpha-glycosides.
    Author: Tatsuta K, Fujimoto K, Kinoshita M.
    Journal: Carbohydr Res; 1977 Mar; 54(1):85-104. PubMed ID: 861969.
    Abstract:
    The key step of the synthesis involves the reaction of glycals [3,4,6-tri-O-acetyl-D-glucal (1), the new glycal derivative 4-O-acetyl-1,5-anhydro-2,6-dideoxy-3-C-methyl-3-O-methyl-L-ribo-hex-1-enitol (2), and 3-acetamido-4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-arabino-hex-1-enitol (3)] with 1.5 molar equivalents of several alcohols in the presence of N-bromosuccinimide in acetonitrile to give mainly the corresponding 2-bromo-2-deoxy-alpha-glycopyranosides (4--21). The glycopyranosides (4-8 and 16-21) from 1 and 3 have the alpha-D-manno configuration and those (10--15) from 2 have the alpha-L-altro configuration. The yields are high from 1, virtually quantitative from 2, and moderate from 3. Debromination of the 2-bromo-2-deoxy compounds with tributylstannane and a radical initiator gives the corresponding 2-deoxy-alpha-glycopyranosides (22-38) in quantitative yields. In particular, the branched-chain glycal 2 reacts with alcohols to give exclusively the corresponding alpha-glycopyranosides (27--32) of cladinose in strikingly high overall yields. The stereoselectivity and regiospecificity of the bromination reaction are described. 1,3-Dibromo-5,5-dimethylhydantoin and N-bromoacetamide are also found to be useful for the reaction.
    [Abstract] [Full Text] [Related] [New Search]