122886-21-9

Basic information

• Product Name: (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate
• Synonyms: (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate
• CAS NO: 122886-21-9
• Molecular Weight: 449.404
• Mol File: 122886-21-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate(122886-21-9)
• EPA Substance Registry System: (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate(122886-21-9)

Safety Data

• Hazardous Substances Data: 122886-21-9(Hazardous Substances Data)

Upstream product

• 122886-20-8 N-tert-butyloxycarbonyl-O-t-butyldimethylsilyl-D-3-iodotyrosine methyl ester 
• 119336-08-2 methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 
• 25799-58-0 (R)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 556-02-5 tyrosine 
• 122908-63-8 N-tert-butyloxycarbonyl-N-methyl-O-t-butyldimethylsilyl-D-3-iodotyrosine methyl ester 
• 478183-68-5 (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 67-56-1 methanol 
• 160531-32-8 (R)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)propanoic acid 

Downstream Products

• 333354-23-7 (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester 
• 333354-37-3 (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid 
• 333354-24-8 (2S,4S,6R,7S,9S)-9-[(R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionyloxy]-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid tert-butyl ester 
• 333354-25-9 (3R,9S,11S,13R,14S,16S)-14-Hydroxy-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione 
• 156953-84-3 (3R,9S,11S,13R,14S,16S)-14-hydroxy-3-[(4-hydroxy-3-iodophenyl)methyl]-4,9,11,13-tetramethyl-16-(propan-2-yl)-1-oxa-4,7-diazacyclohexadecane-2,5,8-trione 
• 122886-23-1 N-tert-butyloxycarbonyl-L-alanyl-N-methyl-D-3-iodotyrosine 
• 119326-48-6 N-tert-butyloxycarbonyl-L-alanyl-N-methyl-D-3-iodotyrosyl-L-alanine methyl ester 
• 122886-22-0 N-tert-butyloxycarbonyl-L-alanyl-N-methyl-O-t-butyldimethylsilyl-D-3-iodotyrosine methyl ester 

Relevant articles and documents

Directed hydrogenations and an Ireland-Claisen rearrangement linked to Evans-Tishchenko chemistry: The highly efficient total synthesis of the marine cyclodepsipeptide doliculide

Two new convergent total syntheses have been developed for the cytotoxic, actin microfilament-stabilizing marine cyclodepsipeptide doliculide (1). A key strategic element of both routes is the establishment of the central stereogenic center of the characteristic polydeoxypropionate stereotriad by means of a hydroxyl-directed catalytic hydrogenation of a trisubstituted double bond. The requisite olefin substrates were obtained through a modified Suzuki-Miyaura coupling or through Ireland-Claisen rearrangement of a propionate ester, respectively; the latter was the direct result of a highly selective Evans-Tishchenko reduction of a hydroxy ketone that had been obtained in a stereoselective Paterson aldol reaction. Doliculide (1) was finally obtained in a total number of 17 or 15 (14) linear steps, respectively, which represents a substantial improvement over previous syntheses of this highly bioactive natural product.