| Author(s) |
Stockton, Kieran
Greatrex, Ben
Taylor, Dennis K
|
| Publication Date |
2014
|
| Abstract |
A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyldialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
|
| Citation |
The Journal of Organic Chemistry, 79(11), p. 5088-5096
|
| ISSN |
1520-6904
0022-3263
|
| Link | |
| Language |
en
|
| Publisher |
American Chemical Society
|
| Title |
Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes
|
| Type of document |
Journal Article
|
| Entity Type |
Publication
|
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