143260-53-1

Basic information

• Product Name: Benzenesulfonamide, N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-phenylethyl]-4-meth yl-, (S)-
• CAS NO: 143260-53-1
• Molecular Formula: C22H33NO3SSi
• Molecular Weight: 419.66
• Mol File: 143260-53-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-phenylethyl]-4-meth yl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-phenylethyl]-4-meth yl-, (S)-(143260-53-1)
• EPA Substance Registry System: Benzenesulfonamide, N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-phenylethyl]-4-meth yl-, (S)-(143260-53-1)

Safety Data

• Hazardous Substances Data: 143260-53-1(Hazardous Substances Data)

Upstream product

• 63-91-2 L-phenylalanine 
• 412908-98-6 (S)-3-[(4-methylphenyl)sulfonyl]-4-phenylmethyl-2-oxazolidinone 
• 98-59-9 p-toluenesulfonyl chloride 
• 51220-86-1 N-(p-toluenesulfonyl)-L-phenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 3182-95-4 L-Phenylalaninol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 82495-70-3 (2S)-2-p-toluenesulfonamido-3-phenylpropanol 

Downstream Products

• 903516-22-3 (S)-4-aza-6-(tert-butyldimethylsilanyloxy)-5-benzyl-4-(p-toluenesulfonyl)hexanal dimethyl acetal 
• 1268630-67-6 cis-5-benzyl-4-(toluene-4-sulfonyl)-2-vinylmorpholine 
• 412909-00-3 (S)-N-[1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]hexadecanamide 
• 60847-18-9 (S)-N-(1-benzyl-2-hydroxyethyl)hexadecanamide 
• 767288-13-1 (5S)-4-aza-5-benzyl-1-hydroxy-7-oxa-4-(p-toluenesulfonyl)cycloheptane 
• 412908-99-7 (S)-N-hexadecanoyl-N-[1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]-p-toluenesulfonamide 

Relevant articles and documents

Synthesis of 2,4-disubstituted piperidines via radical cyclization: Unexpected enhancement in diastereoselectivity with tris(trimethylsilyl)silane

A novel approach to 2,4-disubstituted piperidines is reported, involving the radical cyclization of 7-substituted-6-aza-8-bromooct-2-enoates. Cyclization with tributyltin hydride affords the trans piperidines with trans/cis diastereomeric ratios ranging typically from 3:1 to 6:1. Cyclization with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99:1 in certain cases. The enhancement in diastereoselectivity results from the selective rearrangement of the minor stereoisomer through a cascade process involving radical cyclization to the piperidine radical, 1,5-radical translocation, and attack of the translocated radical onto the sulfonamide with extrusion of SO2 in a Smiles-type rearrangement. Slower trapping of the piperidine radical by tris(trimethylsilyl)silane compared to tributyltin hydride accounts for the occurrence of the rearrangement cascade in the former case.