Use in glycosylation

The pivaloylamidobenzyl group was stable to acetic acid-water-90°, MeOH-NaOMe, iridium-induced allyl isomerization, and to many of the Lewis acids used in glycosylation. ... 

This benzyl ether is partially stable to BF3 Et20 as used in glycosylation reactions and NaOMe, but is not stable to TFA at it for 30 min. 

Figure 7 Common sugars used in glycosylation reactions. /3-Xyiose and /3-fucose (red) are used primariiy by piant and insects, while /3-glucose, /3-mannose, and /3-galactose are used in mammalian systems.

M. Bols, I. Lundt, and E. R. Ottosen, Preparation of 2-, 3-, and 4-deoxy derivatives of L-rhamnose, and derivatives of 2-azido-2-deoxy-L-rhamnose and 2,6-dideoxy-2-fluoro-L-glucose, for use in glycosylation reactions, Carbohydr. Res., 222 (1991) 141-149. 

Mendlik, M.T., Tao, P., Hadad, C.M., Coleman, R.S., and Lowary, T.L. (2006) Synthesis of L-daunosamine and L-ristosamine glycosides via photo-induced aziridination. Conversion to thioglycosides for use in glycosylation reactions. Journal of Organic Chemistry, 71 (21), 8059-8070. 

The hrst synthesis of the sialyl Tn antigen was reported by Ogawa et al. and involved the synthesis of a disaccharide donor consisting of an anomeric trichloroacetimidate of a-NeuNAc-(2 6)-a-D-GalNAc [135]. The donor was then used in glycosylation of Af-(benzyloxycarbonyl)-L-serine... 

Schmidt and co-workers [168,220,221] reported the preparation, and use in glycosylation reactions of several O-hetaryl glycosides, e.g. 458, conveniently prepared by anomeric... 

Even though dendrimer surfaces can be constructed to exhibit all possible functionalities, amine-terminating groups are synthetically more appealing and have been used most extensively. The potentially useful thiolated dendrimers self-oxidize, while carboxylated dendrimers tend to form intramolecular anhydrides once activated. This last situation may cause defects upon carbohydrate attachment. Although alcohols seem also attractive, a priori, their direct use in glycosylation chemistry is hampered by potentially difficult complete anomeric stereocontrol. 

Preparative-scale synthesis of nucleoside triphosphates. Nucleoside triphosphates are utilized as substrates for the biosynthesis of sugar nucleoside phosphates. Practical-scale biosynthesis-based enzymatic preparation of NTPs for use in glycosylations is therefore required. 

Sodium salts of IPs can be used in glycosylation. Sodium hydride was added to 4-chloro-IcP in DMF, the reaction mixture was heated for 5 min at 50 °C, and then 2,3,5-tri-(9-benzoyl-D-arabinofuranosyl chloride was added. The mixture at room temperature for 2h furnished 4-chloro-l-(2,3,5-tri-0-benzyl-D-arabinofuranosyl)-IH-IcP in 89% yield (82USP4315000). 

This kind of compound combines two structural motifs that are of interest, both from the synthetical and biological point of view they are iminocychtols and thioglycosides. The latter type of compounds have been successfully used in glycosylation reactions [52-55], as well as exhibiting interesting biological activities [56,57]. 

The point of interest to synthetic chemists is the range of acceptors and donors that can be used in glycosyl transferase-catalyzed reactions. Fortunately, the specificity of glycosyl transferases is high but not absolute. 

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