1171908-74-9

Basic information

• Product Name: methyl 5-acetamido-2,6-anhydro-4-(benzylamino)-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate
• Synonyms: methyl 5-acetamido-2,6-anhydro-4-(benzylamino)-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate
• CAS NO: 1171908-74-9
• Molecular Weight: 548.752
• Mol File: 1171908-74-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 5-acetamido-2,6-anhydro-4-(benzylamino)-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-acetamido-2,6-anhydro-4-(benzylamino)-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate(1171908-74-9)
• EPA Substance Registry System: methyl 5-acetamido-2,6-anhydro-4-(benzylamino)-7-O-(tert-butyldimethylsilyl)-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate(1171908-74-9)

Safety Data

• Hazardous Substances Data: 1171908-74-9(Hazardous Substances Data)

Upstream product

• 1171908-44-3 methyl 5-acetamido-2,6-anhydro-4-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enoate 
• 100-46-9 benzylamine 

Relevant articles and documents

Useful sialic acid modifications catalyzed by palladium

A stereo- and regioselective allylic substitution on simple N-acetylneuraminic acid (Neu5Ac2en) derivatives that ensures the control of the regio- and stereoselectivity and affords the C-2 or C-4 products with high efficiency, was studied. The Neu5Ac2en substrates were easily prepared from the peracetylated methyl ester 9 obtained by standard treatment overnight of the corresponding Neu5Ac methyl ester. Treatment of acetate 10 under Pd0-catalyzed allylic substitution conditions using sodium dimethylmalonate as a nucleophile failed to provide any alkylation product. The regioselectivity was largely improved to a synthetically useful level when using a more basic monophosphine ligand. A complete reversal of the regioselectivity occurred when the reaction was performed in the presence of bidentate phosphine. Selective transformations of these products provide easy entry to a variety of modified sialic acid derivatives, which can serve as useful sialyl building blocks for biological research.