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A New Strategy for Oligosaccharide Assembly Exploiting Cyclohexane‐1,2‐diacetal Methodology: An Efficient Synthesis of a High Mannose Type Nonasaccharide
Author(s) -
Grice Peter,
Ley Steven V.,
Pietruszka Jörg,
Osborn Helen M. I.,
Priepke Henning W. M.,
Warriner Stuart L.
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030315
Subject(s) - oligosaccharide , glycan , monosaccharide , mannose , cyclohexane , chemistry , glycoprotein , biochemistry , organic chemistry
The high‐mannose nonasaccharide 1 is part of the glycoprotein gp 120 of the viral coat of HIV‐1. The mannan portion of this triantennary glycan was prepared by a number of consecutive glycosidation steps without the need for any protecting‐group manipulation. This was achieved by carefully tuning the reactivity of the glycosyl donors by employing our cyclohexane‐1,2‐diacetal (CDA) methodology. The method was further extended with one‐pot procedures for oligosaccharide synthesis, thus reducing the number of steps to form the protected nonasaccharide 21 from the monosaccharide building blocks to five.