367523-33-9

Upstream product

• 35356-70-8 Methyl 2-acetamidoacrylate 
• 367523-29-3 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 201232-73-7 p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 

Downstream Products

• 493009-57-7 methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of C-glycosyl analogues of phenylalanine

Condensation of 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2- enopyranosyl]-4-bromobenzene (2) with methyl 2-acetamidoacrylate in the presence of Pd(OAc)2, P(C6H4-O-CH3)3, and AgNO3, afforded the unsaturated C-glycosyl enamido ester 3d in 80% yield. Reduction of compound 3d in the presence of [Rh(COD)(R,R)-(Et-DuPHOS)]OTf gave the corresponding unsaturated C-glycosyl (R)-phenylalanine derivative, when the [Rh(COD)(S,S)-(Et-DuPHOS)]OTf catalyst gave the C-glycosyl (S)-phenylalanine derivative, in 67 and 79% yield, respectively. Bis-hydroxylation of compound 4, followed by acetylation afforded the C-mannopyranosyl phenylalanine derivative 5 in overall 30% yield.