220820-69-9

Upstream product

• 115043-29-3 2-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone 
• 100-52-7 benzaldehyde 

Downstream Products

• 503417-12-7 (1R,2R,3S)-3-acetoxy-2-(tert-butyldimethylsilyloxy)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylpropyl acetate 
• 503417-16-1 (2S,3R,4R,5S)-4-(tert-butyldimethylsilyloxy)-3,5-bis(methoxymethoxy)-5-phenylpentane-1,2-diol 
• 503417-14-9 (4S)-2,2-dimethyl-4-[(1R,2R,3S)-2-(tert-butyldimethylsilyloxy)-1,3-bis(methoxymethoxy)-3-phenylpropyl]-1,3-dioxolane 
• 262844-00-8 methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-3-phenylpropionate 
• 262844-04-2 (2R,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-3-phenylpropanoic acid methyl ester 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 247042-37-1 (4S)-2,2-dimethyl-4-[(1R,2R,3S)-2-(tert-butyldimethylsilyloxy)-1,3-dihydroxy-3-phenylpropyl]-1,3-dioxolane 

Relevant academic research and scientific papers

Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions

We have investigated the formation of various metal enolates of 1-O- silylated erythrulose 3,4-acetonides. We were able to prepare boron enolates using Brown's dicyclohexylboron chloride / tertiary amine system. When these enolates were allowed to react w

Influence of the protecting groups on the syn/anti stereoselectivity of boron aldol additions with erythrulose derivatives. A theoretical and experimental study

We have investigated a series of aldol additions of protected L-erythrulose derivatives mediated by dicyclohexyl boron chloride. The syn/anti stereoselectivity has been found to depend on the type of protecting groups on the hydroxyl functions at C-3 and

Erythrulose derivatives as functionalized chiral d3 and d4 synthons

Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d3 or d4 synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide.

Aldol reactions with erythrulose derivatives: Stereoselective synthesis of differentially protected syn-α,β-dihydroxy esters

Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2- syn/1,3-syn stereoisomer. Thro

Boron aldol additions with erythrulose derivatives: Dependence of stereoselectivity on the type of protecting group

Boron aldol additions of 1-O-silylated 3,4-di-O-benzyl- and 3,4-di-O-benzoyl-L-erythrulose and achiral aldehydes using dicyclohexylboron chloride have been investigated. The dibenzyl derivative gave syn/syn stereoisomers with high stereoselectivity, whereas the dibenzoyl derivative gave syn/anti stereoisomers. It is believed that, while the dibenzoyl erythrulose gives rise to the E enolate in the presence of dicyclohexylboron chloride, as usually observed with this reagent, only the Z enolate is formed in the case of the dibenzyl derivative.