253676-17-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 253676-18-5 (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 253676-15-2 (3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol 
• 140200-05-1 tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 

Downstream Products

• 253676-34-5 (2R,3R)-3-[(tert-Butyldimethylsiloxy)methyl]-2-ethynyl-N-(2,4,6-trimethylphenylsulfonyl)aziridine 
• 253676-19-6 (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol 

Relevant academic research and scientific papers

Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

Two convenient methods for the synthesis of chiral 2-ethynylaziridines from natural α-amino acids are described. Sodium hydride-promoted aziridination of mesylates of 4-arylsulfonylamino-2-bromoalk-2-en-1-ols yields trans-2-(1-bromovinyl)aziridines in a highly stereoselective manner, and subsequent dehydrobromination of the aziridines by potassium tert-butoxide gives separable stereoisomeric mixtures of trans- and cis-2-ethynylaziridines in enantiomerically pure forms (>98% ee). Simple synthesis of 2-ethynylaziridines with high optical purities (91-98% ee) from chiral amino alcohols bearing an ethynyl group under Mitsunobu conditions is also presented. The Royal Society of Chemistry 1999.