186803-48-5

Usage

Chemical Properties

Pale Yellow Solid

Upstream product

• 27304-20-7 2,3-O-cyclohexylidene-γ-D-ribonolactone 
• 123168-27-4 2,3-O-cyclohexylidene-D-ribofuranose 
• 108-94-1 cyclohexanone 

Downstream Products

• 186790-80-7 2,3-(cyclohexylidenedioxy)-4-hydroxy-4-(2-propyloxy)butanoic acid lactone 
• 111005-68-6 (-)-2,3-(cyclohexylidenedioxy)-1-<(p-tolylsulfonyl)oxy>cyclopent-4-ene 
• 111005-65-3 (-)-2,3-(cyclohexylidenedioxy)-4-cyclopentenone 
• 293738-45-1 (2R,3S)-2,3-O-cyclohexylidene-1,4-di-O-p-toluenesulfonyl-butan-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Reinvestigation of the synthesis of (2R,3R) 2,3-(cyclohexylidenedioxy)-4-cyclopentenone as possible building block for the synthesis of carbocyclic nucleosides

An in depth study of the four-steps synthesis of (2R,3R) 2,3-(cyclohexylidenedioxy)-4-cyclopentenone (5) from D-ribonolactone (1) is described. From these experiments we must conclude that the overall yield reported in the literature (65%) is overestimated. All compounds have been throughly investigated by 1H- and 13C-NMR spectroscopy.

A new synthesis of D-ribonolactone from D-ribose by pyridinium chlorochromate oxidation

2,3-O-Cyclohexylidene-D-ribonolactone is prepared directly from 2,3-O-cyclohexylidene-D-ribose by pyridinium chlorochromate (PCC) oxidation in 55-60% yield.