552888-50-3

Upstream product

• 225663-00-3 O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 95319-02-1 N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester 
• 23680-31-1 BOC-O-benzyl-L-serine 

Downstream Products

• 225663-06-9 O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 1356389-32-6 O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-N-(tert-butoxycarbonyl)-L-serine tert-butyl ester 
• 1356389-34-8 O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-N-(tert-butoxycarbonyl)-L-serine 
• 1356389-35-9 O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine 
• 1356389-36-0 (3S,5aR,6R,7R,8R,9aS)-3-[N-(tert-butoxycarbonyl)amino]-6,7-bis(benzyloxy)-8-[(benzyloxy)methyl]octahydropyrano[2,3-b][1,5]oxazepin-4-one 
• 1356389-33-7 O-[(2-(fluorenyl-9-methoxycarbonyl)amino)-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl]-L-serine 

Relevant academic research and scientific papers

A convenient synthesis of pyrano[2,3-b][1,5]oxazepines by ring closure of O-glycosyl amino acids

N-Boc-protected serine and threonine esters could be readily added to 2-nitroglycals, affording exclusively α- and β-anomers with galacto- and gluco-configuration, respectively. Nitro group reduction to the amino group and also ester cleavage led to compo

O-glycosyl amino acids by 2-nitrogalactal concatenation - Synthesis of a Mucin-type O-glycan

Base-promoted Michael-type addition of N-Boc- and N-Fmoc-protected serine and threonine esters to 2-nitrogalactal derivatives 2 and 26 led highly selectively to α-glycosides 4a-d and 27a,c, respectively. Ensuing transformation of threonine derivative 4d a

A novel and efficient route towards α-GalNAc-Ser and α-GalNAc-Thr building blocks for glycopeptide synthesis

Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri- O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro- α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2- nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D- galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.