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Multigram-scale synthesis of L,D-heptoside using a Fleming-Tamao oxidation promoted by mercuric trifluoroacetate
- Source :
- Carbohydrate Research. 432:71-75
- Publication Year :
- 2016
- Publisher :
- Elsevier, 2016.
-
Abstract
- An efficient multigram-scale synthesis of methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside from methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reactions. The resulting scaffold was used as a precursor to design a small library of clickable L-heptosides. This study shows that the use of mercuric bistrifluoroacetate is required both to accelerate and to cleanly perform the Fleming-Tamao oxidation, without side-reactions.
- Subjects :
- Molecular Structure
010405 organic chemistry
Chemistry
Homologation
Organic Chemistry
Lipopolysaccharide
Mercury
General Medicine
Heptoses
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Analytical Chemistry
Grignard addition
Swern oxidation
Trifluoroacetic Acid
Organic chemistry
Click Chemistry
Glycosides
Fleming–Tamao oxidation
Heptose
Fleming-Tamao oxidation
Oxidation-Reduction
Subjects
Details
- Language :
- English
- ISSN :
- 1873426X and 00086215
- Volume :
- 432
- Database :
- OpenAIRE
- Journal :
- Carbohydrate Research
- Accession number :
- edsair.doi.dedup.....68b1f1cc4503e6eb096a8d85264b16b2