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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Synthesis of methyl glycosides of beta-(1----6)-linked D-galactobiose, galactotriose, and galactotetraose having a 3-deoxy-3-fluoro-beta-D-galactopyranoside end-residue.

Methyl 2,4-di-O-acetyl-3-deoxy-3-fluoro-beta-D-galactopyranoside was synthesized by sequential tritylation, acetylation, and detritylation of methyl 3-deoxy-3-fluoro-beta-D-galactopyranoside, and used as the initial nucleophile in the synthesis of methyl beta-glycosides of (1----6)-beta-D-galacto-biose, -triose (20), and -tetraose (22) having a 3-deoxy-3-fluoro-beta-D-galactopyranoside end-residue. The extension of the oligosaccharide chains, to form the internal units in 20 and 22, was achieved by use of 2,3,4-tri-O-acetyl-6-O-bromoacetyl-alpha-D-galactopyranosyl bromide as a glycosyl donor, and mercuric cyanide or silver triflate as the promotor. While fewer by-products were formed in the reactions involving mercuric cyanide, the reactions catalyzed by silver triflate were stereospecific and yielded only the desired beta (trans) products.[1]

References

  1. Synthesis of methyl glycosides of beta-(1----6)-linked D-galactobiose, galactotriose, and galactotetraose having a 3-deoxy-3-fluoro-beta-D-galactopyranoside end-residue. Kovác, P., Glaudemans, C.P. Carbohydr. Res. (1985) [Pubmed]
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