666237-89-4

Upstream product

• 666237-84-9 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose 
• 97673-01-3 1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 666237-80-5 6-O-tert-butyldimethylsilyl-[(S)-1,2-O-(1-ethoxyethylidene)]-α-D-glucopyranose 

Downstream Products

• 666238-07-9 6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose 
• 666238-16-0 methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranuronate 
• 666238-01-3 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyl bromide 
• 666238-11-5 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose 
• 666238-29-5 methyl 2-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyluronate bromide 

Relevant academic research and scientific papers

Comparison of Several Glucuronate Glycosyl Donors

Methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D- glucopyranuronate (12), methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]- α-D-glucopyranuronate (14), methyl 2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranuronate bromide (15), methyl (2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranosyl)uronate trichloroacetimidate (17), and methyl (2,3,4-tri-O-benzyl-α/β-D-glucopyranosyl)uronate trichloroacetimidate (30) were synthesized and used as glycosyl donors. Glycosylation reactions of 12 with (5-R)-2,3,4,5-tetrahydro-5-trityloxymethyl-2- furanone (32) and 14,15,17 with the corresponding (5-R)-2,3,4,5-tetrahydro-5- hydroxymethyl-2-furanone (31) provided the exclusively β-linked glucuronide 33 in 69%, 28%, 45%, and 71% yield, respectively. The coupling of donor 30 with acceptor 31 furnished the glucuronated lactone 35 in 70% yield with a surprisingly high content (20%) of the undesired α-linked sugar residue. The structure of 33 was proved by NMR and X-ray diffraction studies. In a model reaction a complete deprotection procedure of the glucuronic acid lactone conjugation was demonstrated.