79184-52-4

Upstream product

• 79184-49-9 methyl 3,4-anhydro-α-D-tagatofuranoside 
• 32087-60-8 2,3-O-isopropylidene-1,6-bis-O-(p-tolylsulphonyl)-β-D-fructofuranose 
• 13403-14-0 methyl α-D-fructofuranoside 
• 76227-30-0 methyl 4-O-methylsulphonyl-1,6-bis-O-(p-tolylsulphonyl)-β-D-fructofuranoside 
• 76234-86-1 2,3-O-isopropylidene-5-O-methylsulphonyl-1,6-bis-O-(p-tolylsulphonyl)-β-D-fructofuranose 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Epoxidaton using Triphenylphosphine-Diethyl Azodicarboxylate: Synthesis of Methyl 3,4-Anhydro-α- and -β-D-tagatofuranosides

Facile syntheses of the title compounds have been achieved by the one-step reaction of methyl α- or β-D-fructofuranoside with triphenylphosphine and diethyl azodicarboxylate in dimethylformamide; no blocking groups were necessary.

Epoxidations with Triphenylphosphine and Diethyl Azodicarboxylate. Part 1. Synthesis of Methyl 3,4-Anhydro-D-tagatofuranosides

Treatment of methyl β-D-fructofuranoside (6) with triphenylphosphine and diethyl azodicarboxylate in dimethylformamide gives a high yield of methyl 3,4-anhydro-β-D-tagatofuranoside (5); no blocking of the hydroxy-groups at C-1 and C-6 is necessary.The structure of the product was confirmed by an X-ray structural study of its 1,6-bis-O-(p-tolylsulphonyl) derivative and by an unambiguous synthesis.A similar reaction of methyl α-D-fructofuranoside yielded the 3,4-anhydro-α-D-tagatofuranoside.The reaction mechanism is discussed.