126587-61-9

Upstream product

• 116939-86-7 ((benzyloxy)carbonyl)-L-leucyl-L-proline 
• 126587-60-8 N,O-dimethyltyrosine-O-Boc-threonine-OSEM 
• 76513-69-4 (2-trimethylethylsilylethoxy)methyl chloride 
• 129919-84-2 Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine 
• 126587-59-5 Z-N,O-dimethyltyrosine-O-Boc-threonine-OSEM 
• 49761-04-8 N-(benzyloxycarbonyl)-L-leucyl-L-proline methyl ester 
• 1164-16-5 Z-L-Tyr-OH 
• 2592-18-9 Boc-Thr-OH 
• 2018-66-8 Z-Leu-OH 
• 192211-84-0 (S)-2-(Benzyloxycarbonyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 118171-80-5 (2S)-3-[4-(methyloxy)phenyl]-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid 
• 126587-71-1 Boc-threonine [(2-trimethylsilyl)ethoxy]methyl ester 

Downstream Products

• 129919-84-2 Z-leucylprolyl-N,O-dimethyltyrosine-O-Boc-threonine 
• 250039-52-2 L-leucyl-L-prolyl-N,O-dimethyl-L-tyrosine-N-boc-O-SEM-L-threonine 
• 148339-15-5 C₅₈H₁₀₁N₅O₁₅Si 
• 126587-63-1 N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-hydroxy-1-isop 
• 1053630-19-5 C₆₆H₁₀₇N₅O₁₆Si 
• 126587-64-2 N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3S)-1-isopropyl-2- 
• 126587-62-0 N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4- 
• 325687-71-6 [5-isobutyl-8,13-diisopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-4,7,10,15,19,22-hexaoxo-12-triisopropylsilanyloxy-eicosahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacycloheneicosen-16-yl]-carbamic acid tert-butyl ester 
• 345664-71-3 N-Z-prolyl-[Hiv²] didemnin A 
• 325687-70-5 C₆₆H₁₀₉N₅O₁₆Si₂ 
• 1053247-83-8 4-amino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester 
• 779313-73-4 (5S,8S,12S,13R,16S,17R,20S,22aS)-16-Amino-13-((S)-sec-butyl)-12-hydroxy-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-tetradecahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacyclohenicosene-4,7,10,15,19,22-hexaone 
• 258339-38-7 (-)-tamandarin B 
• 250039-54-4 C₆₇H₁₁₁N₅O₁₆Si₂ 

Relevant academic research and scientific papers

Mild, selective cleavage of amino acid and peptide β-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide

Magnesium bromide etherate has been previously shown to cleave β-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Troc carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis.

SYNTHETIC STUDIES OF DIDEMNINS. IV. SYNTHESIS OF THE MACROCYCLE

A stereocontrolled route to the 23-membered macrocycle found in the didemnins is described.