165876-49-3

Upstream product

• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 149099-13-8 (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile 
• 170305-51-8 Methyl (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxylate 
• 201536-71-2 1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 165657-75-0 (4R)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 
• 149099-14-9 (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde 
• 165657-74-9 (2R)-4-iodo-1,2-O-isopropylidenebutane-1,2-diol 

Downstream Products

• 170305-52-9 (2R,5R,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>pentane-1,2,5-triol 

Relevant academic research and scientific papers

Stereoselective Additions of Chiral, Functionalized Organozinc Reagents to Achiral and Chiral Aldehydes: a Matched-Mismatched Case in Organozinc Chemistry

The additions of the enantiomerically pure organozinc reagents 17 and 33 to the THF-aldehyde 1 in the presence of the monodentate Lewis acid boron trifluoride-ether give the nonchelation-controlled addition products 7 and 36, respectively (stereoselectivity 95:5, 86:14).These results provide a route to oligo(tetrahydrofuran)s with the relative stereochemistry trans-syn-cis.A stereodirecting effect of the chiral center in the organozinc reagent 17 is found, leading to simple diastereoselectivies in the reaction with achiral aldehydes and to a matched-mismatched case in the reaction with the chiral aldehyde 1. - Key Words: Addition, stereoselective, nonchelation-controlled / Reagent, organozinc / Stereodifferentiation, double / Oligo(tetrahydrofuran)

Tetrahydrofuran-podands, stereoselective synthesis of trans-2,5-oligo-tetrahydrofurans

Enantiomerically pure THF-podands 1 were synthesized along a linear route starting from lactone 3. A high degree of stereochemical control was achieved by chelation controlled addition of the functionalized Grignard reagent 7 to α-alkoxy-aldehydes of type 6.