A general approach to carbocyclic sugar analogs: preparation of a carbocyclic analog of beta-D-fructofuranose.
The development and execution of the first examples of a new and general approach to carbocyclic analogs of carbohydrates ("pseudo-sugars") is presented. Complete experimental details for the preparation of the carbocyclic analog of beta-D-fructofuranose 6-phosphate are described for the first time. In the conclusion, the success of the synthetic strategy is analyzed and an approach to retrosynthetic analysis based on "unitive synthons" is offered for consideration.
Gaudino
J J
JJ
Department of Chemistry, University of Pittsburgh, Pennsylvania 15260.
Wilcox
C S
CS
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D015394:Molecular Structure; D009904:Optical Rotation; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry
D002241:Carbohydrates; D003511:Cyclohexanols; D013403:Sugar Phosphates; C067759:5-carbafructofuranose 6-phosphate