205641-95-8

Upstream product

• 1215-59-4 5-benzyloxy-1H-indole 
• 13154-24-0 triisopropylsilyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 205641-94-7 5-(benzyloxy)-1-(triisopropylsilyl)-1H-indole 
• 205641-88-9 (1S,2S,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methoxymethyl-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of conformationally restrained, β-substituted derivatives of l-tryptophan via lewis acid-catalyzed reaction of 2,3-aziridino-β-d-lyxo-furanosides with 1-(trialkylsilyl)indoles

Reaction of 1-(triisopropylsilyl)indole (or its 5-benzyloxy derivative) with tert-butyldimethylsilyl N-(tert-butyloxycarbonyl)-2,3-aziridino-2,3-dideoxy5-O-methyl- (or benzyl-)-β-D-lyxofuranoside in the presence of boron trifluoride etherate gave, regio- and stereospecifically, the corresponding protected 2-amino-3-(3-indolyl)arabinofuranoside derivatives. These could be transformed, after desilylation, oxidation and removal of the Boc group, into 2-amino-3-(3-indolyl)arabinonolactone derivatives. The latter represent novel examples of conformationally restrained analogues of L-tryptophan as well as precursors of optically pure β-substituted L-tryptophans.