294846-96-1

Basic information

• Product Name: Acetic acid, diazo[(1,1-dimethylethyl)dimethylsilyl]-, phenylmethyl ester
• CAS NO: 294846-96-1
• Molecular Formula: C15H22N2O2Si
• Molecular Weight: 290.437
• Mol File: 294846-96-1.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid, diazo[(1,1-dimethylethyl)dimethylsilyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, diazo[(1,1-dimethylethyl)dimethylsilyl]-, phenylmethyl ester(294846-96-1)
• EPA Substance Registry System: Acetic acid, diazo[(1,1-dimethylethyl)dimethylsilyl]-, phenylmethyl ester(294846-96-1)

Safety Data

• Hazardous Substances Data: 294846-96-1(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 52267-51-3 benzyl diazoacetate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 443988-55-4 benzyl 2-[tert-butyl(dimethyl)silyl]-2-oxoacetate 
• 294847-05-5 tert-butoxycarbonylamino-(tert-butyl-dimethyl-silanyl)-acetic acid benzyl ester 

Relevant articles and documents

Organocatalyzed Direct Aldol Reaction of Silyl Glyoxylates for the Synthesis of α-Hydroxysilanes

A novel organocatalyzed direct aldol reaction of aldehydes to silyl glyoxylates is disclosed. This method provides an efficient route to α-hydroxysilanes with excellent enantioselectivities (up to 99% ee) and high diastereoselectivities (up to >20:1 dr). In the new activation model of silyl glyoxylates, the hydrogen bond is critical to the reaction. A carbonyl group directly attached to silicon in acylsilanes could be activated by coordination to the proton of hydroxyl and carboxylic acid via a hydrogen bond. Moreover, commercially available cis-l-4-hydroxyproline is an ideal organocatalyst for activating both aldehydes and acylsilanes.

Synthesis and use of α-silyl-substituted α-hydroxyacetic acids

(matrix presented) Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-silyl-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral α-silyl-substituted α-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.