180776-35-6

Upstream product

• 85992-74-1 2-Acetylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester 
• 262423-15-4 Methyl 6-[benzyl(benzyloxycarbonyl)amino]-5,7-dideoxy-2,3-O-isopropylidene-α-L-talo-octofuranoside 
• 262423-12-1 Methyl 6-(benzyloxycarbonylamino)-5,6-dideoxy-2,3-O-isopropylidene-L-glycero-α-L-talo-octofuranoside 
• 262423-13-2 Methyl 6-(benzyloxycarbonylamino)-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-octo-7-enofuranoside 
• 262423-14-3 Methyl 6-[benzyl(benzyloxycarbonyl)amino]-5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-L-talo-oct-7-enofuranoside 

Relevant academic research and scientific papers

Synthetic studies of nucleoside antibiotics: A formal synthesis of (+)-sinefungin

A formal synthesis of (+)-sinefungin 1 is described. The C-6′ and C-9′ stereogenic centers of sinefungin were constructed stereoselectively by efficient catalytic asymmetric syntheses. The key strategy for the construction of the C-6′ stereocenter involve

Total synthesis of (+)-sinefungin

Sinefungin (1) a nucleoside antibiotic isolated from Streptomyces has been synthesized from D-ribose. Both the C-6 and C-9 stereogenic centers were constructed by efficient asymmetric syntheses. The C-6 amine stereochemistry was set by a highly diastereoselective allylation (> 99% de) of a (1S,2R)-1-amino-2-indanol-derived oxazolidinone 9 followed by a Curtius rearrangement of 11 to 12. The C-9 amino acid stereochemistry of sinefungin (1) was established by a rhodium chiral bisphosphine-catalyzed asymmetric hydrogenation of an α-(acylamino)acrylate derivative. The anomeric adenosylation of the mixture of anomeric acetates 20 in the presence of C-6 urethane NH was found to be extremely difficult. Conversion of the C-6 urethane NH as its N-benzyl derivative 21 was necessary prior to the adenosylation reaction. Successful adenosylation was effectively carried out by Vorbruggen's protocol utilizing persilylated N6-benzoyladenine and trimethylsilyl triflate.