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Direct, microwave-assisted substitution of anomeric nitrate-esters
- Source :
- Carbohydrate research. 442
- Publication Year :
- 2017
-
Abstract
- A series of carbohydrate 2-azido-1-nitrate-esters, protected at the C-3, C-4, and C-6 positions, were hydrolyzed thermally under reagent free conditions. This preliminary result was extended to direct exchange of the 1-nitrate-ester modality for alcohol, alkoxy, and azide coupling partners with minimal purification. While direct glycosylation of nitrate esters ultimately proved unsuccessful, we have demonstrated that an anomeric nitrate-ester can be converted directly to a trichloroacetimidate in a short and simple one-pot procedure, bypassing lower yielding two-step sequences.
- Subjects :
- Azides
Anomer
Glycosylation
010405 organic chemistry
Hydrolysis
Organic Chemistry
Alcohol
Esters
General Medicine
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Analytical Chemistry
chemistry.chemical_compound
chemistry
Reagent
Alkoxy group
Carbohydrate Conformation
Organic chemistry
Azide
Nitrate ester
Microwaves
Subjects
Details
- ISSN :
- 1873426X
- Volume :
- 442
- Database :
- OpenAIRE
- Journal :
- Carbohydrate research
- Accession number :
- edsair.doi.dedup.....0cd0a78f2c288988db69b156be1e910c