138891-99-3

Basic information

• Product Name: N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine
• Synonyms: N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine
• CAS NO: 138891-99-3
• Molecular Weight: 524.054
• Mol File: 138891-99-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(138891-99-3)
• EPA Substance Registry System: N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine(138891-99-3)

Safety Data

• Hazardous Substances Data: 138891-99-3(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 126402-89-9 2,3,4-tri-O-pivaloyl-β-D-arabinopyranosylamine 
• 138891-96-0 2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl azide 
• 138892-04-3 α-D-Arabinopyranosyl azide 

Downstream Products

• 686341-86-6 2,2-Dimethyl-propionic acid (2S,3S,4R,5R)-2-[(R)-2-(4-chloro-phenyl)-4-oxo-3,4-dihydro-2H-pyridin-1-yl]-4,5-bis-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-3-yl ester 
• 138892-01-0 N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile 
• 138892-01-0 N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-D-(4-chlorophenyl)glycinonitrile 

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.

Stereoselective synthesis of L-amino acids via Strecker and Ugi reactions on carbohydrate templates

L-Amino acid derivatives are stereoselectively synthesized in high yield using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine or 2,3,4-tri-O-pivaloyl-β-L-fucopyranosylamine as the chiral auxiliary in Strecker and Ugi reactions.