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Intrinsic Issues in the Assembly of 1,2‐Linked Oligosaccharides
Author(s) -
Kashiwagi Gustavo A.
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000107
Subject(s) - chemistry , glycosidic bond , context (archaeology) , linkage (software) , stereochemistry , computational biology , biochemistry , gene , enzyme , paleontology , biology
This review aims to highlight common issues involved in the assembly of 1,2‐linked oligosaccharides. There is extensive literature on the subject, but most of the publications only address general oligosaccharides. Construction of 1,2‐glycosidic linkage has an additional and intrinsic complexity due to its glycosylated O ‐2 position. Elongation of the fragment from reducing end curtails the possibility of using O ‐2 participating groups in the donor. The 2‐ O ‐glycosylated donors used in this context or in a convergent approach lead to the principal stereocontrol loss when 1,2‐ trans gluco type or manno type linkage are targets. Only non‐reducing end elongation strategy can ensure 1,2‐ trans linkage, but following a more expensive and cumbersome route. Archetypical cases where the convergent approach drove to a stereocontrol loss are presented. The perspective of this analysis attempts to complement Paulsen, Boons and Demchenko's masterworks about strategies in oligosaccharides synthesis.