204913-05-3

Upstream product

• 66026-10-6 N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 
• 1005-56-7 phenylcarbonochloridothioate 

Downstream Products

• 204913-10-0 Ethyl 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl)propanoate 
• 716377-12-7 benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-3-C-(penta-2',4'-dienyl)-α-D-glucopyranoside 
• 331241-41-9 3-(Benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl)propanoic acid 
• 716377-08-1 benzyl 2-acetamido-3-C-allyl-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of C-3 branched allyl and pentadienyl glucosamines via radical coupling of sugar-thionocarbonates

The intermolecular AIBN-promoted free radical reaction of glucosamine thionocarbonates as radical donors, and allyl or pentadienyl-tributyltin reagents gave the expected C-3 branched sugar derivatives in good yield and with total equatorial selectivity. Copyright

Synthesis of normuramic acid Carba analog and its glycopeptide derivative resistant to β-elimination splitting of the side chain

Carba analogs of normuramic acid, i.e., 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-iso-propylidene-α-D-glucopyranosid-3-yl) propanoic acid derivatives (nitrile or esters) 3a-3c were prepared by addition of radicals generated from benzyl 2-acetamido-2-deoxy-4,6-O-iso-propylidene-3-O-[(methylsulfanyl)thiocarbonyl]- (2a) or -3-O-(phenoxythiocarbonyl)-α-D-glucopyranoside (2b) with Bu3SnH to acrylonitrile or acryl esters. Alkaline hydrolysis of ethyl ester 3c afforded 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl) propanoic acid (5). Coupling of acid 5 with L-2-aminobutanoyl-D-isoglutamine benzyl ester trifluoroacetate and subsequent deprotection of the intermediate 6 furnished N-[3-(2-acetamido-2,3-dideoxy-α-D-glucopyranosid-3-yl)propanoyl]-L-2- amino-butanoyl-D-isoglutamine (7).