141395-63-3

Basic information

• Product Name: N-Benzylidene-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine
• Synonyms: N-Benzylidene-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine
• CAS NO: 141395-63-3
• Molecular Weight: 489.609
• Mol File: 141395-63-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-Benzylidene-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylidene-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(141395-63-3)
• EPA Substance Registry System: N-Benzylidene-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(141395-63-3)

Safety Data

• Hazardous Substances Data: 141395-63-3(Hazardous Substances Data)

Upstream product

• 138891-96-0 2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl azide 
• 138892-04-3 α-D-Arabinopyranosyl azide 
• 126402-89-9 2,3,4-tri-O-pivaloyl-β-D-arabinopyranosylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 2935-35-5 (S)-2-phenylglycine 
• 141330-82-7 Diethyl α-<(2,3,4-Tri-O-pivaloyl-β-D-arabinopyranosyl)amino>benzylphosphonate 
• 141330-80-5 Diethyl α-<(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)amino>benzylphosphonate 
• 141330-81-6 Diethyl α-<(2,3,4-Tri-O-pivaloyl-β-D-arabinopyranosyl)amino>benzylphosphonate 
• 141330-74-7 Diethyl α-<(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)amino>benzylphosphonate 
• 138892-00-9 N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-phenylglycinonitrile 
• 138892-00-9 N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-D-phenylglycinonitrile 

Relevant articles and documents

Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary

Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino Mannich-Michael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydropiperidinones. Electrophilic substitution at the enamine structure afforded 5-nitro- and 5-halogen dehydropiperidinones of which the latter were applied in palladium-catalyzed coupling reactions. The absolute configuration of the obtained products was proven by NMR and X-ray structure analysis as well as by syntheses of the alkaloids (+)-coniine and (+)-dihydropinidine.