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Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide
- Source :
- Org Lett
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- The first synthesis of the tetrasaccharide fragment of the anthracycline natural product Arugomycin is described. A reagent controlled dehydrative glycosylation method involving cyclopropenium activation was utilized to synthesize the α-linkages with complete anomeric selectivity. The synthesis was completed in 20 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.
- Subjects :
- Glycosylation
Anomer
Natural product
010405 organic chemistry
Longest linear sequence
Stereochemistry
Organic Chemistry
Oligosaccharides
010402 general chemistry
01 natural sciences
Biochemistry
Article
0104 chemical sciences
chemistry.chemical_compound
Carbohydrate Sequence
chemistry
Reagent
Yield (chemistry)
Deoxy Sugars
Tetrasaccharide
Anthracyclines
Physical and Theoretical Chemistry
Selectivity
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 22
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....f85295e53afbc6276c05f5035028a2ca
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c01153