1219619-07-4

Upstream product

• 100-52-7 benzaldehyde 
• 42206-19-9 Diethyl-((E)-styryl)-borane 
• 87727-28-4 (S)-2-tert-butyl-dimethyl-silanyloxy propanal 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 119404-55-6 2-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 
• 95832-97-6 (S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-one 
• 116696-50-5 Acetic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester 
• 103635-88-7 (E)-(S)-4-Hydroxy-1-phenyl-pent-1-en-3-one 

Downstream Products

• 6837-05-4 (+/-)-2-phenyl-1,4-butanediol 
• 22927-18-0 2-Phenyl-4-hydroxy-butyraldehyd 
• 1219619-32-5 (3S,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (R)-O-Mosher ester 
• 1219619-31-4 (3S,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (S)-O-Mosher ester 

Relevant academic research and scientific papers

Stem Cell Culture Methods

The invention provides methods for reversibly inhibiting stem cell differentiation wherein a compound of formula (I) is contacted with a stem cell. The invention further provides a method for preparing a culture medium, a culture medium supplement and a composition comprising a compound of formula (I).

Overriding felkin control: A general method for highly diastereoselective chelation-controlled additions to α-silyloxy aldehydes

According to the Felkin-Anh and Cram-chelation models, nucleophilic additions to α-silyloxy aldehydes proceed through a nonchelation pathway due to the steric and electronic properties of the silyl group, giving rise to Felkin addition products. Herein we describe a general method to promote chelationcontrol in additions to α-silyloxy aldehydes. Dialkylzincs, functionalized dialkylzincs, and (E)-disubstituted, (E)-trisubstituted, and (Z)-disubstituted vinylzinc reagents add to silyl-protected α-hydroxy aldehydes with high selectivity for chelation-controlled products (dr of 10:1 to 20:1) in the presence of alkylzinc halides or triflates, RZnX. With the high functional group tolerance of organozinc reagents, the mild Lewis acidity of RZnX, and the excellent diastereoselectivities favoring the chelation-controlled products, this method will be useful in the synthesis of natural products. A mechanism involving chelation is supported by (1) NMR studies of a model substrate, (2) a dramatic increase in reaction rate in the presence of an alkylzinc halide, and (3) higher diastereoselectivity with larger alkyl substituents on the α-carbon of the aldehyde. This method provides access to chelation-controlled addition products with high diastereoselectivity previously unavailable using achiral organometallic reagents.

SYNTHESIS OF 1-SUBSTITUTED (S)-4-ACETOXY-1-PENTEN-3-ONES USING (S)-LACTIC ACID AS A CHIRAL SOURCE AND THEIR SYNTHETIC REACTIONS

Ylide reaction of (S)-3-acetoxy-1-triphenylphosphoranylidene-2-butanone, derived from (S)-lactic acid, with aldehydes gives 1-substituted (S)-4-acetoxy-1-penten-3-one derivatives, which are shown to be transformed into useful chiral compouds by stereosele