201232-87-3

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 201232-73-7 p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 171082-23-8 4-t-butylphenyl4, 6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 201233-15-0 (2R,3S,6R)-6-(4-tert-Butyl-phenoxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol 

Downstream Products

• 368452-23-7 (2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)benzene 
• 368452-29-3 (2,3-dideoxy-β-D-erythro-hexanopyranosyl)benzene 
• 3682-06-2 (2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)benzene 
• 891785-95-8 (6-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)benzene 

Relevant academic research and scientific papers

Synthesis and Mesogenic Properties of Enantiopure Trioxadecalin Derivatives Bearing a n-Alkylphenyl Substituent

Reaction of pseudo-glucal 1 with Grignard reagents derived from various 4-n-alkyl-4-bromobenzene in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated β-C-aryl glycosides 2. Desilylation and hydrogenation of these compo

Stereochemistry in palladium- and nickel-catalyzed addition of phenylmagnesium bromide to unsaturated carbohydrates

Palladium complex PdCl2(dppf) and nickel complex NiCl2(dppe) catalyze cross-coupling of unsaturated aryloxy carbohydrates with phenylmagnesium bromide. The nickel catalyst leads to inversion of configuration at the anomeric center wh

Synthesis of α- and β-C-Aryl Δ2-Glycopyranosides from p-tert-Butylphenyl Δ2-Glycopyranosides via Grignard Reagents

Treatment of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1aα) or the 4,6-di-O-(tert-butyldimethylsilyl) analogue (1bα) with various functionalized arylmagnesium bromides in the presence of a catalytic amount of PdCl2(dppf) at 25°C in THF afforded the corresponding unsaturated C-arylglycosides 2-14 having the α-configuration in quite good yields. Benzyl-, allyl-, and vinylmagnesium bromides gave also the corresponding unsaturated α-C-glycosides 15-18, although in lower yields. When the same reaction was performed in the presence of NiCl2(dppe) as the catalyst at -40°C, only the formation of the corresponding unsaturated C-arylglycosides having the β-configuration was observed. As expected, reaction of phenylmagnesium bromide with p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (1aβ) in the presence of NiCl2(dppe) gave only the unsaturated β-C-phenylglycoside 2aβ, while palladium-catalyzed reaction led to the preponderant formation of C-phenylglycoside 2aα. Reaction of PhMgBr with p-tert-butylphenyl 4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (20) afforded stereospecifically the unsaturated α- and β-C-phenylglycoside 25 in the presence of PdCl2-(dppf) and NiCl2(dppe), respectively.