138584-48-2

Upstream product

• 81801-09-4 4-O-benzyl-2,3-O-isopropylidene-D-threose 
• 138584-47-1 5-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-2,3-dideoxy-D-galacto-oct-2-enono-1,4-lactone 

Downstream Products

• 138584-50-6 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-D-threo-L-talo-octo-pyranose 
• 138584-56-2 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-D-threo-L-talo-octo-pyranose 
• 138584-49-3 2,3,4-tri-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-D-threo-L-talo-octono-1,4-lactone 

Relevant academic research and scientific papers

Highly stereoselective total synthesis of octopyranose derivatives

A couple of enantiomeric octopyranoses, endowed with differentiated protective groups, namely the L-threo-D-talo-and D-threo-L-talo- octose derivatives L-6 and D-6, were synthesized from the enantiomers of threose L-1 and D-1 in ca 10% overall yield in five individual steps. The synthetic plan emphasizes the value of 2-(trimethylsiloxy)furan (TMSOF) as four-carbon homologative reactant of homochiral aldehyde precursors en route to higher-carbon monosaccharide units.