1333040-71-3

Upstream product

• 1096706-74-9 (2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanal 
• 1096707-44-6 methyl (2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanoate 
• 1096707-45-7 (2R,3R,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentan-1-ol 
• 1333041-55-6 (-)-(2R,3R,4R,5S,6S)-3,5,7-tris(benzyloxy)-2,4,6-trimethylheptan-1-ol 
• 1333041-51-2 (+)-(2S,3S,4S,5S,6S)-methyl 3,5,7-tris(benzyloxy)-2,4,6-trimethylheptanoate 
• 1333041-47-6 (-)-(3R,4R,5R,6S,7S,8S)-methyl 5,7,9-tris(benzyloxy)-2-bromo-3-hydroxy-2,4,6,8-tetramethylnonanoate 
• 1333040-68-8 (+)-(2S,3S,4S,5S,6S)-3,5,7-tris(benzyloxy)-2,4,6-trimethylheptanal 

Downstream Products

• 1333041-61-4 (+)-(4S,5S,6S,7S,8S,9S,10S)-ethyl 7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanoate 
• 1333041-63-6 (+)-methyl 2-bromo-2-((2S,5S,6S)-5-methyl-6-((2S,3S,4S,5S,6S)-3,5,7-tris(benzyloxy)-4,6-dimethylheptan-2-yl)tetrahydro-2H-pyran-2-yl)propanoate 
• 1333041-65-8 (+)-(2S,3S,4S,5S,6S,7S,8S)-5,7,9-tris(benzyloxy)-2,4,6,8-tetramethyl-3-(triethylsilyloxy)nonan-1-ol 
• 1333040-74-6 (+)-(2R,3R,4S,5S,6S,7S,8S)-5,7,9-tris(benzyloxy)-2,4,6,8-tetramethyl-3-(triethylsilyloxy)nonanal 
• 1333041-59-0 (+)-(4S,5S,6S,7S,8S,9S,10S,E)-ethyl 7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undec-2-enoate 
• 1333041-67-0 (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecan-1-ol 
• 1333040-78-0 (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal 
• 1333041-53-4 (+)-(2R,3R,4S,5S,6S,7S,8S)-methyl 5,7,9-tris(benzyloxy)-2,4,6,8-tetramethyl-3-(triethylsilyloxy)nonanoate 

Relevant academic research and scientific papers

A bidirectional approach to the synthesis of polypropionates: Synthesis of C1-C13 fragment of zincophorin and related isomers

The structure-activity study of a bioactive natural product containing polypropionate subunits requires that its stereoisomers also be evaluated. Therefore, a general approach to synthesize these motifs is necessary. We describe herein the synthesis of the C1 - C13 polypropionate subunit of zincophorin and isomers there of using a two-reaction sequence: an aldol reaction using a mixture of tetrasubstituted enoxysilanes and a hydrogen-transfer reaction, both under Lewis acid control. Selection of the appropriate Lewis acid dictates the stereochemical outcome of these reactions. From a tactical standpoint, this study shows how a polypropionate sequence can be read and constructed in two directions, either the east-west or the west-east approaches. The choice of the optimal route is influenced by the number of complexation sites that can interfere in the aldol step under bidentate Lewis acid control.