138328-85-5

Upstream product

• 18933-62-5 methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 83532-13-2 methyl 3-(benzyloxycarbonyl)amino-4-(diphenylphosphinoylmethoxy)methyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 83532-11-0 methyl 3-(benzyloxycarbonyl)amino-2,3,6-trideoxy-α-arabino-hexopyranosid-4-ulose 
• 83532-10-9 methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 67693-33-8 methyl-3-amino-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 
• 138456-68-5 methyl 3-(benzyloxycarbonyl)amino-4-(E)-methoxymethylene-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose

A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.