478693-67-3

Upstream product

• 142041-83-6 methyl 2,3,4-trideoxy-2-C-methyl-6-O-benzyl α-D-threo-hex-3-enopyranoside 
• 68907-47-1 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside 
• 478693-74-2 Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester 
• 478693-62-8 methyl 6-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside 

Downstream Products

• 478693-75-3 (2S,5S,6S)-6-Methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde 

Relevant academic research and scientific papers

The carbohydrate-sesquiterpene interface. A zirconocene-mediated synthesis of (+)-epiafricanol from D-glucose

A total synthesis of (+)-epiafricanol (6) has been readily achieved from D-glucose. The tricyclic alcohol target was arrived at by first forming methyl 6-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside (12) and converting this intermediate into methyl 2-C-methyl-2,3,4-trideoxy-α-D-threo-hexopyranoside (14). There followed a series of steps resulting in extension of the side chain to give the isopropenyl pyranoside 9. This advanced intermediate was subjected to zirconocene-promoted ring contraction, which gave rise to 8 and set the stage for conversion to 7. This tertiary carbinol was transformed into 6 by sequential ring-closing metathesis and stereodirected Simmons-Smith cyclopropanation.