625109-58-2

Upstream product

• 129029-85-2 (2RS)-3-(tert-butyldiphenylsilyloxy)-2-methylpropanol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 123284-89-9 (+/-)-2-methyl-3-[(tert-butyldiphenylsilyl)oxy]propanal 
• 535-11-5 Ethyl 2-bromopropionate 
• 17360-25-7 N-(p-toluenesulfonyl)-L-valine 
• 153645-08-0 2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene 

Downstream Products

• 625109-61-7 ethyl (2S,3R,4S)-5-(tert-butyldiphenylsiloxy)-2-bromo-3-methoxymethoxy-2,4-dimethylpentanoate 
• 475051-47-9 (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanal 
• 475051-58-2 (2S,3S,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanol 
• 475051-60-6 (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol 
• 475051-59-3 (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid methyl ester 
• 625109-63-9 ethyl (2R,3R,4S)-5-(tert-butyldiphenylsiloxy)-3-hydroxy-2,4-dimethylpentanoate 
• 630117-27-0 ethyl (2S,3R,4S)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate 
• 625109-62-8 ethyl (2R,3R,4S)-5-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,4-dimethylpentanoate 
• 625109-64-0 ethyl (2R,3R,4S)-3-(tert-butyldimethylsiloxy)-5-(tert-butyldiphenylsiloxy)-2,4-dimethylpentanoate 

Relevant academic research and scientific papers

Regulated-stereoselective construction of thirteen stereogenic centers necessary for the frame of (+)-discodermolide, based on iterative Lewis acid-promoted aldol reactions

The segments C1-C13 and C15-C 21 containing the 13 stereogenic centers required for the frame of (+)-discodermolide were synthesized in good to excellent enantio- and diastereoselectivities from a common racemic

Diastereoselective radical debromination approach toward divergent syntheses of syn- and anti-propionate units, coupled with enantioselective and/or diastereoselective Lewis acid-promoted aldol reactions

A practical methodology directed to the enantioselective synthesis of polypropionate backbones, available for the synthesis of polyketide natural products, has been developed by iterative enantio- and diastereoselective Lewis acid-promoted aldol reactions, followed by diastereoselective radical debromination reactions. A chiral oxazaborolidinone-promoted aldol reaction of a racemic aldehyde, derived from 2-methyl-1,3-propanediol, with a silylketene acetal from ethyl 2-bromopropionate, resulted in highly enantioselective formation of the corresponding bromo aldol adduct, followed by radical debromination with Bu3SnH in the presence of Et3B to divergently give syn- and anti-propionate aldols, which are versatile stereotriads. Furthermore, elongation of the propionate units has also been achieved: the BF3·OEt2-promoted aldol reaction of chiral syn- and anti-α-methyl-β-protected-oxy aldehydes with the silyl nucleophile proceeded with essentially complete syn-selectivity while the TiCl4-promoted aldol reaction resulted in fairly good anti-selectivity. The resulting bromo aldol adducts were divergently debrominated by the radical reduction to give a complete set of stereotetrads.