225663-00-3

Upstream product

• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 211621-55-5 3,4,6-tri-O-benzyl-2-nitro-D-galactal 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 95319-02-1 N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester 

Downstream Products

• 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 
• 552888-50-3 O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 

Relevant academic research and scientific papers

N-heterocyclic carbene catalyzed stereoselective glycosylation of 2-nitrogalactals

An efficient N-heterocyclic carbene catalyzed glycosylation of 2-nitrogalactals with alcohols and phenol has been developed for the first time. A wide variety of 1,2-cis-2-nitroglycosides can be obtained with good to excellent yields and high to excellent

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.