302964-51-8

Basic information

• Product Name: (S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester
• Synonyms: (S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester
• CAS NO: 302964-51-8
• Molecular Weight: 587.454
• Mol File: 302964-51-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester(302964-51-8)
• EPA Substance Registry System: (S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester(302964-51-8)

Safety Data

• Hazardous Substances Data: 302964-51-8(Hazardous Substances Data)

Upstream product

• 79677-62-6 (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 501-53-1 benzyl chloroformate 
• 70-78-0 3-Iodo-L-tyrosine 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 
• 16874-12-7 Tyr(tBu) 
• 100-39-0 benzyl bromide 
• 870456-12-5 (S)-N-benzyloxycarbonyl-3-iodotyrosine tert-butyl ester 

Downstream Products

• 302964-55-2 (S)-4-benzyloxy-3-(1-(3-bromo-2-hydroxyphenyl)prop-2-enyl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 
• 302964-50-7 (S)-4-benzyloxy-3-(7-bromo-2-oxo-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 
• 302964-56-3 (S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 
• 302964-54-1 (S)-4-benzyloxy-3-(3-(2-bromophenoxy)propenyl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 
• 302964-53-0 (S)-4-benzyloxy-3-(3-bromopropenyl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 
• 302964-52-9 (S)-4-benzyloxy-3-(3-hydroxypropenyl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester 

Relevant articles and documents

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement

A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalysed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A.

Studies towards the synthesis of diazonamide A. Synthesis of a tyrosine-derived benzofuranone

The benzofuranone 2, a potential intermediate for the synthesis of the marine natural product diazonamide A 1, has been synthesised in eight steps from the N-protected tyrosine ester 3. (C) 2000 Elsevier Science Ltd.