52745-75-2

Upstream product

• 51152-15-9 dimethyl (1S,2S)-trans-cyclopropane-1,2-dicarboxylate 
• 82442-59-9 ((1S*,2S*)-cyclopropane-1,2-diyl)dimethanol 
• 821-11-4 trans-butene-1,4-diol 
• 14399-53-2 bis(iodomethyl)zinc 
• 142096-80-8 (-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane 
• 454476-70-1 [(1R,2S)-2-((1E,5E)-2,6,10-Trimethyl-undeca-1,5,9-trienyl)-cyclopropyl]-methanol 
• 58931-16-1 (R)-1-benzyloxypent-4-en-2-ol 
• 142176-75-8 (Z)-(R)-1-benzyloxy-6-(trimethyl-silanyl)-hex-4-en-2-ol 
• 188610-46-0 1-((((1R,2S)-2-vinylcyclopropyl)methoxy)methyl)benzene 
• 534584-66-2 (1R,2R)-2-((benzyloxy)methyl)cyclopropanecarbaldehyde 
• 337983-98-9 (R)-7-benzyloxymethyl-2,2-dimethyl-2,3,6,7-tetrahydro-[1,2]oxasilepine 
• 337983-96-7 Allyl-((R)-1-benzyloxymethyl-but-3-enyloxy)-dimethyl-silane 
• 34202-45-4 (1R,2R)-1,2-cyclopropanedicarboxylic acid 
• 613261-14-6 (-)-(R,R)-cyclopropane-1,2-dicarboxylic acid ethyl ester 

Downstream Products

• 142096-80-8 (-)-(1R,2R)-2-benzyloxymethyl-1-hydroxymethylcyclopropane 

Relevant academic research and scientific papers

Recombinant squalene synthase. A mechanism for the rearrangement of presqualene diphosphate to squalene

Squalene synthase (SQase) catalyzes the condensation of two molecules of farnesyl diphosphate (FPP) to form presqualene diphosphate (PSPP) and the subsequent rearrangement and NADPH-dependent reduction of PSPP to squalene (SQ). These reactions are the fir

Highly stereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with methyl (diazoacetoxy)acetate catalyzed by a chiral ruthenium(II) complex

Tantalizing triangles: The title reaction gives bicarbonyl cyclopropane products that can lead to versatile intermediates with high yields and stereoselectivities. This system was also applied to the enantioselective total synthesis of spiro cyclopropane oxindole, an HIV-1 nonnucleoside reverse transcriptase inhibitor. Copyright

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.

Synthetic methodology for the construction of structurally diverse cyclopropanes

Practical and efficient routes for the stereoselective conversion of homoallylic alchols to diastereomerically pure cis-, trans-1,2-disubstituted, and 1,2,3-trisubstituted cyclopropanes have been developed. The routes are highlighted by olefin metathesis

Iterative cyclopropanation: A concise strategy for the total synthesis of the hexacyclopropane cholesteryl ester transfer protein inhibitor U-106305

The first enantioselective total synthesis of the hexacyclopropane natural product U-106305, which is produced by Streptomyces sp. UC 11136, is described in full detail. Considerations on the biosynthesis of U-106305 and its close resemblance to the penta

A Catalytic Enantioselective Reaction Using a C2-Symmetric Disulfonamide as a Chiral Ligand: Simmons-Smith Cyclopropanation of Allylic Alcohols by the Et2Zn-CH2I2-Disulfonamide System

A catalytic and enantioselective Simmons-Smith cyclopropanation of an allylic alcohol was developed by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 4.

Enzymes in Organic Synthesis. 24. Preparations of Enantiomerically Pure Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Monocyclic Meso Diols

Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidation of monocyclic meso diols provides a direct and convenient one-step route to a broad range of chiral γ-lactones of value as synthons in asymmetric synthesis.The general applicability of the method is demonstrated by oxidations of cis-1,2-bis(hydroxymethyl) substrates of the cyclohexyl, cyclohexenyl, cyclopentyl, cyclobutyl, cyclopropyl, and dimethylcyclopropyl series.For each diol, oxidation of the hydroxymethyl group attached to the S chiral center occurs exclusively, and the pure γ-lactone products are isolated in high (68-90percent) yields and of 100percent ee.In contrast, the enzyme does not exhibit significant enantiomeric selectivity in its catalysis of oxidations of the corresponding racemic trans diols.The stereospecificities observed, or lack thereof, are as predicted by the active-site model.