72399-19-0

Upstream product

• 622-33-3 N-benzyloxyamine 
• 123-38-6 propionaldehyde 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Downstream Products

• 91078-06-7 1-Benzyloxy-4-ethyl-3,3-dimethyl-azetidin-2-one 
• 1421611-50-8 N-n-propyl-O-benzyl-N-(β-D-glucopyranosyl)hydroxylamine 
• 1421611-57-5 N-n-propyl-O-benzyl-N-(β-D-galactopyranosyl(1→2)β-D-glucopyranosyl)hydroxylamine 
• 126227-46-1 (1-Benzyloxyamino-propyl)-phosphonic acid 

Relevant academic research and scientific papers

Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles

Saturated azacycles are commonly encountered in bioactive compounds and approved therapeutic agents. The development of methods for functionalization of the α-methylene C-H bonds of these highly privileged building blocks is of great importance, especially in drug discovery. While much effort has been dedicated toward this goal by using a directed C-H activation approach, the development of directing groups that are both general as well as practical remains a significant challenge. Herein, the design and development of novel amidoxime directing groups is described for Ir(I)-catalyzed α-C(sp3)-H alkylation of saturated azacycles using readily available olefins as coupling partners. This protocol extends the scope of saturated azacycles to piperidines, azepane, and tetrahydroisoquinoline that are incompatible with our previously reported directing group. A variety of olefin coupling partners, including previously unreactive disubstituted terminal olefins and internal olefins, are compatible with this transformation. The selectivity for a branched α-C(sp3)-alkylation product is also observed for the first time when acrylate is used as the reaction partner. The development of practical, one-step installation and removal protocols further adds to the utility of amidoxime directing groups.

Alkoxyamino glycoside acceptors for the regioselective synthesis of oligosaccharides using glycosynthases and transglycosidases

Alkoxyamino derivatives of oligosaccharides have been synthesized by enzymatic synthesis using a glycosynthase and a transglycosidase. The chemoselective assembly of unprotected oligosaccharides bearing glucose at the reducing end with N-alkyl-O-benzylhydroxylamine provides sugar derivatives that are good acceptors for enzymatic synthesis using either glycosynthase or transglycosidase. Furthermore, this method affords the possibility of controlling the regioselectivity of coupling depending on the nature of the alkoxyamino substituent and provides high-yield coupling of sugars without the need for complex protecting group chemistry.