188909-26-4

Basic information

• Product Name: Ethanone, 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[(1,1-dimethylethyl)diphenylsil yl]oxy]-, O-(phenylmethyl)oxime, (1Z)-
• CAS NO: 188909-26-4
• Molecular Formula: C30H37NO4Si
• Molecular Weight: 503.714
• Mol File: 188909-26-4.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[(1,1-dimethylethyl)diphenylsil yl]oxy]-, O-(phenylmethyl)oxime, (1Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[(1,1-dimethylethyl)diphenylsil yl]oxy]-, O-(phenylmethyl)oxime, (1Z)-(188909-26-4)
• EPA Substance Registry System: Ethanone, 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[(1,1-dimethylethyl)diphenylsil yl]oxy]-, O-(phenylmethyl)oxime, (1Z)-(188909-26-4)

Safety Data

• Hazardous Substances Data: 188909-26-4(Hazardous Substances Data)

Upstream product

• 622-33-3 N-benzyloxyamine 
• 147107-70-8 1-O-t-butyldiphenylsilyl-3,4-O-isopropylidene-L-erythrulose 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Downstream Products

• 188909-33-3 O-Benzyl-N-[(R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentyl]-hydroxylamine 
• 211044-98-3 (4R,5R)-3-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-phenyl-oxazolidin-2-one 
• 188909-48-0 (4R)-3-benzyloxy-4-phenyl-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxazolidin-2-one 
• 188909-50-4 (4R)-3-benzyloxy-4-phenyl-4-methoxycarbonyl-1,3-oxazolidin-2-one 
• 211188-24-8 (4R)-3-benzyloxy-4-phenyl-4-((1R)-1,2-dihydroxyethyl)-1,3-oxazolidin-2-one 
• 211044-94-9 (2R,3R)-3,4-O-isopropylidene-2-(N-benzyloxyamino)-2-phenylbutane-1,3,4-triol 
• 188909-47-9 (4R)-3-benzyloxy-4-methyl-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxazolidin-2-one 
• 188909-49-1 (4R)-3-benzyloxy-4-methyl-4-methoxycarbonyl-1,3-oxazolidin-2-one 
• 188909-53-7 (2R)-3-hydroxy-2-(N-benzyloxyamino)-2-phenylpropionic acid 
• 211188-18-0 (4R)-3-benzyloxy-4-methyl-4-((1R)-1,2-dihydroxyethyl)-1,3-oxazolidin-2-one 
• 211044-91-6 (2R,3R)-3,4-O-isopropylidene-2-(N-benzyloxyamino)-2-methylbutane-1,3,4-triol 
• 188909-51-5 (2R)-3-hydroxy-2-(N-benzyloxyamino)-2-methylpropionic acid 
• 188909-37-7 O-Benzyl-N-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-ethyl]-hydroxylamine 
• 188909-41-3 O-Benzyl-N-[(R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-enyl]-hydroxylamine 

Relevant articles and documents

Diastereoselectivity of the reactions of organolithium reagents with protected erythrulose oximes

The addition of organolithium reagents to the C=N bond of several erythrulose-derived chiral (E)- and (Z)-ketoxime ethers has been shown to be highly diastereoselective in the case of the (E)-isomers. Chelated and nonchelated transition states have been proposed to rationalize these results, with additional support of computational methods.

Diastereoselective additions of organolithium reagents to the C=N bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-aminoacids

The addition of organolithium reagents to the C=N bond of several erythrulose-derived chiral (E)- and (Z)-ketoxime ethers has been shown to be highly diastereoselective for the (E)-isomers. A chelated transition state has been proposed to explain this result. The addition products were converted into the two α,α-disubstituted α-aminoacids (R)-2-(-)-methylserine and (R)-(+)-2-phenylserine.