421556-69-6

Basic information

• Product Name: (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester
• Synonyms: (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester
• CAS NO: 421556-69-6
• Molecular Weight: 545.44
• Mol File: 421556-69-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester(421556-69-6)
• EPA Substance Registry System: (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester(421556-69-6)

Safety Data

• Hazardous Substances Data: 421556-69-6(Hazardous Substances Data)

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 421556-68-5 (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-iodophenyl)alanine methyl ester 
• 100-39-0 benzyl bromide 
• 119140-66-8 N-Cbz-O-benzyl-L-tyrosine methyl ester 
• 13512-31-7 N-(benzyloxycarbonyl)-L-tyrosine methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 73183-34-3 bis(pinacol)diborane 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 79677-60-4 (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester 
• 501-53-1 benzyl chloroformate 
• 70-78-0 3-Iodo-L-tyrosine 
• 60-18-4 L-tyrosine 

Downstream Products

• 262854-05-7 TMC-95B 
• 421556-74-3 2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester 
• 421556-72-1 4-[(7-{2-benzyloxy-5-[2-benzyloxycarbonylamino-2-(1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 421556-73-2 2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester 
• 421556-71-0 (S)-4-[7-{2-Benzyloxy-5-[(S)-2-benzyloxycarbonylamino-2-((S)-1-tert-butoxycarbonyl-2-carbamoyl-ethylcarbamoyl)-ethyl]-phenyl}-2-oxo-1,2-dihydro-indol-(3E)-ylidenemethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid 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.

Preparation of selectively protected L-dopa derivatives: Oxidation of tyrosine-3-boronates

Conversion of 3-iodo-L-tyrosine to protected tyrosine-3-boronate esters, followed by oxidation with hydrogen peroxide, provides a mild and efficient method for the preparation of selectively protected L-dopa derivatives.