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Peer Reviewed Journal
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Glinschert, Anja; Oscarson, Stefan
2015
September
Carbohydrate Research
Synthesis of four (4''-, 2''-, 2'-, and 6-) monodeoxy analogs of the trisaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-ManpOMe recognized by Calreticulin/Calnexin
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Synthesis of four (4''-, 2''-, 2'-, and 6-) monodeoxy analogs of the trisaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-ManpOMe recognized by Calreticulin/Calnexin
Routes for efficient synthesis of four (4''-, 2''-, 2'-, and 6-) monodeoxy analogs of the trisaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-ManpOMe have been developed.  For the introduction of the 2'- and 2''-deoxy motifs the most efficient way was to use a 1,2-di-bromo-mannosyl donor in silver triflate-promoted couplings to construct the α-glycosidic linkage followed by redn. of the 2-bromo-function to a 2-deoxy motif at the di- or trisaccharide level.  In contrast, the 4''- and 6-deoxy functions were introduced already at the monosaccharide stage.  The most challenging part of the syntheses was the stereoselective formation of the non-reducing end cis-α-D-glucosidic linkages.  The established α-directing effect of a 3-O-acetyl group in glucosyl donors was explored but the magnitude of the effect was variable and dependent on donor/acceptor structure and nature of promoter and an optimization had to be made for each individual glycosylation.
http://www.ncbi.nlm.nih.gov/pubmed/26257376
10.1016/j.carres.2015.07.006
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