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https://hdl.handle.net/2440/102092
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Type: | Journal article |
Title: | Synthesis of allo-and epi-inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes |
Author: | Stockton, K. Greatrex, B. Taylor, D. |
Citation: | Journal of Organic Chemistry, 2014; 79(11):5088-5096 |
Publisher: | American Chemical Society |
Issue Date: | 2014 |
ISSN: | 0022-3263 1520-6904 |
Statement of Responsibility: | Kieran P. Stockton, Ben W. Greatrex, and Dennis K. Taylor |
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-alkyl-dialdoses 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. |
Rights: | © 2014 American Chemical Society |
DOI: | 10.1021/jo500645z |
Published version: | http://dx.doi.org/10.1021/jo500645z |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 3 |
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