Common side reactions of the glycosyl donor in chemical glycosylation.

Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals

Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses

The first polymer-assisted solution-phase synthesis of deoxyglycosides.

Stereoselective Synthesis of Oligo‐α(2,8)‐3‐deoxy‐D‐manno‐2‐octulosonic Acid Derivatives

Addition Reactions of Glycal Esters: Access to Glycosyl Donors of Kdo, d-glycero-d-talo- and d-glycero-d-galacto-2-Octulosonic Acid Residues

Addition reactions of O-acetylated glycal esters of Kdo mono-, α-(2→8)- and α-(2→4)- linked Kdo disaccharide derivatives 1a - c with NIS in acetic acid afforded good yields of trans-diaxial as well as minor amounts of trans-diequatorial and cis-configured 2-O-acetyl-3-deoxy-3-iodo derivatives, which were efficiently reduced with Bu3SnH/AIBN to give the corresponding per-O-acetylated Kdo methyl ester derivatives. Similar reactions of 1a with NBS or NCS furnished the trans-diaxial 2-O-acetyl-3-bromo-3-deoxy- as well as 3-chloro-3-deoxy derivatives as the main products. Reaction of 1a with NBS in aqueous MeCN provided the 2,3-trans-bromohydrin derivative 11c, which upon treatment with DBU in MeCN gave the elimination product 11 and the α-2,3-anhydro derivative 12 as a suitable donor of glycosides with D-glycero-D-talo- or D-glycero-D-galacto configuration, respectively.

Gregor Balint

Papers

Addition Reactions of Glycal Esters: Access to Glycosyl Donors of Kdo, d-glycero-d-talo- and d-glycero-d-galacto-2-Octulosonic Acid Residues

Addition Reactions of Glycal Esters: Access to Glycosyl Donors of Kdo, D-glycero-D-talo- and D-glycero-D-galacto-2-Octulosonic Acid Residues.