333354-23-7

Basic information

• Product Name: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester
• Synonyms: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester
• CAS NO: 333354-23-7
• Molecular Weight: 648.654
• Mol File: 333354-23-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester(333354-23-7)
• EPA Substance Registry System: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester(333354-23-7)

Safety Data

• Hazardous Substances Data: 333354-23-7(Hazardous Substances Data)

Upstream product

• 4530-20-5 BOC-glycine 
• 333354-36-2 (R)-3-(3-Iodo-4-triisopropylsilanyloxy-phenyl)-2-methylamino-propionic acid methyl ester 
• 122886-21-9 (R)-methyl 3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)-2-(methylamino)propanoate 
• 160531-32-8 (R)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)-3-iodophenyl)propanoic acid 
• 478183-68-5 (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 25799-58-0 (R)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 13154-24-0 triisopropylsilyl chloride 
• 333354-22-6 2-(tert-butoxycarbonyl-methyl-amino)-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester 
• 333354-35-1 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester 
• 119336-08-2 methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 

Downstream Products

• 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 
• 333354-26-0 Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl 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 
• 333354-37-3 (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid 

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.