221015-76-5

Upstream product

• 127244-81-9 methyl 2,3-O-isopropylidene-α-D-mannofuranoside 5,6-O-cyclic sulfate 
• 221015-74-3 methyl 5-O-tert-butyldiphenylsilyl-6,7,8-trideoxy-2,3-O-isopropylidene-α-D-manno-oct-7-ynofuranoside 

Relevant academic research and scientific papers

Regioselective synthesis of 6-alkynyl-6-deoxy and pseudo-C- disaccharides derivatives of mannofuranose via a 5,6-cyclic sulfate

C-6 opening of a 5,6-cyclic sulfate derivative of mannofuranoside 1 with acetylenic anion generated from oct-1-yne or phenylethyne gave corresponding 6-alkynyl-6-deoxy derivatives 2 and 3 respectively. The reaction of 5,6- cyclic sulfate 1 with lithium acetylide derived from monosaccharide led to pseudo-C-disaccharide 5. A one-pot procedure was achieved using lithium acetylide in THF/HMPA, to prepare symmetric pseudo-C-disaccharide 7. This method, used with a 5,6-cyclic sulfate derivative of glucofuranose 11 with the acetylide anion derived from mannofuranose 9, gave the corresponding nonsymmetric pseudo-C-disaccharide 13.