159495-21-3

Upstream product

• 108-94-1 cyclohexanone 
• 22250-06-2 1,2-O-Cyclohexylidene-α-D-xylofuranose 
• 98-88-4 benzoyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 120964-98-9 methyl 2,3,5-tri-O-benzoyl-αβ-D-xylbofuranoside 
• 16162-35-9 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-xylofuranose 
• 20822-87-1 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-xylofuranose 

Relevant academic research and scientific papers

DIRECT PREPARATION OF 1,2:3,5-DI-O-CYCLOHEXYLIDENE-α-D-XYLOFURANOSE FROM CORNCOBS AND ITS CONVERSION TO 1-O-ACETYL2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE

A novel synthesis of 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (I) has been described starting from 1,2:3,5-di-O-cyclohexylidene-α-D-xylofuranose (II), obtained directly from the crude xylose syrup originated from corncobs.Partial acid hydrolysis of II gave 1,2-O-cyclohexylidene-α-D-xylofuranose (III).Selective benzoylation of primary C-5 hydroxyl group of III followed by tosylation of C-3 hydroxyl group afforded IV in an overall yield of 67percent.Mild acid methanolysis of IV gave the corresponding methyl xylofuranosides V which further benzoylated to afford 2,5-di-O-benzoyl derivatives VI in 65percent yield.Solovolysis of VI in 95percent DMF gave a mixture of 2,5- and 3,5-di-O-benzoylribofuranosides VII, which were subsequently converted into the corresponding tribenzoates VIII.An acetolysis of VIII afforded I in an overall yield of 96percent related to VI.