194146-32-2

Basic information

• Product Name: 4-Hexen-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(diphenylmethylene)amino]-, (2S,3S,4E)-
• CAS NO: 194146-32-2
• Molecular Formula: C25H35NO2Si
• Molecular Weight: 409.644
• Mol File: 194146-32-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Hexen-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(diphenylmethylene)amino]-, (2S,3S,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hexen-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(diphenylmethylene)amino]-, (2S,3S,4E)-(194146-32-2)
• EPA Substance Registry System: 4-Hexen-3-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(diphenylmethylene)amino]-, (2S,3S,4E)-(194146-32-2)

Safety Data

• Hazardous Substances Data: 194146-32-2(Hazardous Substances Data)

Upstream product

• 115134-32-2 methyl (S)-2-(diphenylmethylideneamino)propanoate 
• 350031-15-1 (E)-(3-bromoallyloxy)(tert-butyl)(dimethyl)silane 
• 116381-84-1 (E)-1-tert-butyldimethylsilyloxy-3-iodo-2-propene 

Downstream Products

• 194146-48-0 2,2-Dimethyl-propionic acid (1R,2R,3R)-1-[(S)-1-(benzhydrylidene-amino)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2,3-bis-methoxymethoxy-butyl ester 
• 243662-98-8 5-amino-1-O-tert-butyldimethylsilyl-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol 
• 194146-50-4 (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-2,3-bis-methoxymethoxy-4-pivaloyloxy-1-hexanal 
• 194146-54-8 5-amino-N-diphenylmethylene-4-O-pivaloyl-5-deoxy-L-galactitol 
• 194146-56-0 (2S,3R,4R,5S)-5-amino-N-diphenylmethylene-4-pivaloyloxy-2,3,4-trihydroxy-hexan-1-al 
• 194146-58-2 N-diphenylmethyl-4-O-pivaloyl-L-(-)-1-deoxyfuconojirimycin 
• 243663-16-3 (2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol 
• 117821-10-0 1,5-Didesoxy-1,5-imino-N-methyl-L-fucit 
• 99212-30-3 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.