194146-56-0

Basic information

• Product Name: (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al
• Synonyms: (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al
• CAS NO: 194146-56-0
• Molecular Weight: 411.498
• Mol File: 194146-56-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al(194146-56-0)
• EPA Substance Registry System: (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al(194146-56-0)

Safety Data

• Hazardous Substances Data: 194146-56-0(Hazardous Substances Data)

Upstream product

• 243662-98-8 5-amino-1-O-tert-butyldimethylsilyl-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol 
• 194146-46-8 (4S,5S,2E)-5-amino-1-O-tert-butyldimethylsilyl-N-diphenylmethylene-4-O-pivaloyl-2-hexen-1,4-diol 
• 194146-32-2 (4S,5S,2E)-5-amino-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-hexen-1,4-diol 
• 3282-30-2 pivaloyl chloride 
• 194146-54-8 5-amino-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol 

Downstream Products

• 99212-30-3 deoxyfuconojirimycin 
• 117821-10-0 1,5-Didesoxy-1,5-imino-N-methyl-L-fucit 
• 243663-16-3 (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol 
• 194146-58-2 N-diphenylmethyl-4-O-pivaloyl-L-(-)-1-deoxyfuconojirimycin 

Relevant articles and documents

Glycosidase inhibitors: Synthesis of enantiomerically pure aza-sugars from Schiff base amino esters via tandem reduction-alkenylation and osmylation

Nitrogen-in-the-ring 'aza-sugars' have been synthesized in enantiomerically pure form from the amino acid L-alanine in excellent overall yield. The O'Donnell's Schiff base of L-alanine methyl ester 9a was converted to aza-sugar L-fuco-1-deoxy-nojirimycin, 18, and to the epimer L-gulo-1- deoxy-nojirimycin, 20, in eight steps. The overall yields were 20 and 29%, respectively. The methodology for the efficient generation of silyl- and benzyl-protected (E)-3-lithio-2-propen-1-ols, and the use of these alkenyllithiums with iBu5Al2H as nucleophiles in the threo-selective tandem reduction-alkenylation of the Schiff base esters is described. Osmium- catalyzed cis-oxygenation of the resulting olefin products was selective for the galacto (fuco) amino polyols in all cases for the acyclic olefins, and was gulo-selective for the cyclic D-4,5-dihydropyridine pivalate, 17c. TEMPO- NaOCl was selective for oxidation of the primary position of the acyclic Schiff bases, and allowed for minimal protection/deprotection of the intermediates. The resulting N-benzhydryl heterocycles were easily deprotected with H2-Pd at atmospheric pressure.