102208-95-7

Upstream product

• 489473-44-1 1-phenyl-oct-2-ene-1,7-dione 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 102108-39-4 (2S,6S)-(E)-2-(cis-6-methyltetrahydropyran-2-yl)-1-phenylethene 
• 102208-94-6 (2R,6S)-(trans-6-methyltetrahydropyran-2-yl)acetophenone 
• 99212-19-8 (S)-(+)-5-chloropentan-2-ol 
• 102208-93-5 (2R,6S)-(E)-2-(trans-6-methyltetrahydropyran-2-yl)-1-phenylethene 
• 102108-37-2 (7S)-(+)-3-acetoxy-1-phenyl-7-(tetrahydropyranyl-2-oxy)oct-1-ene 
• 5891-21-4 5-chloro-2-pentanone 
• 18653-60-6 2-acetoxy-6-methyltetrahydropyran 
• 102108-38-3 (7S)-(+)-3-acetoxy-7-hydroxy-1-phenyloct-1-ene 
• 102108-36-1 (7S)-(+)-3-hydroxy-1-phenyl-7-(tetrahydropyranyl-2-oxy)oct-1-ene 
• 24156-97-6 (2S)-(+)-5-chloro-2-(tetrahydropyranyl-2-oxy)pentane 

Downstream Products

• 102208-96-8 phenyl (2S,6S)-(cis-6-methyltetrahydropyran-2-yl)acetate 

Relevant academic research and scientific papers

Alcohol Dehydrogenase-triggered Oxa-Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans

An alcohol dehydrogenase-mediated asymmetric reduction and subsequent intramolecular oxa-Michael reaction has been developed for the preparation of tetrahydropyrans (or oxanes) and tetrahydrofurans, in excellent conversion, yield and high enantiomeric and diastereomeric excess. To highlight the utility of the methodology, we report the synthesis of an analogue of the fungal antioxidant brocaketone A. Also described is the preparation of the (–)-(R,R)-enantiomer of the natural product, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

Gold(I)/(III)-catalyzed synthesis of cyclic ethers; Valency-controlled cyclization modes

Strategic use of oxophilic (hard) gold(III) and π-philic (soft) gold(I) catalysts provides access to two types of cyclic ethers from propargylic alcohols. Thus, heating propargylic alcohols with an oxophilic gold(III) catalyst (AuBr3) results i

TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS

Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R

Selective Deoxygenation of Unsaturated Carbohydrates with Pd(0)/Ph2SiH2/ZnCl2. Total Synthesis of (+)-(S,S)-(6-Methyltetrahydropyran-2-yl)acetic Acid

Highly chemoselective reductive cleavage of allylic acetates of 1,2- and 2,3-unsaturated monosaccharides was achieved by a three-component reducing system comprised of diphenylsilane, a soluble palladium(0) catalyst, and catalytic amounts of zinc chloride.It was demonstrated that hydride substitution proceeds with absolute inversion of configuration at the carbon, implying that hydride is initially transferred to palladium and from there to the allylic ligand.The usefulness of the new chiral building blocks thus formed was demonstrated by the total synthesis of the civet constituent, (+)-(2S,6S)-cis-(6-methyltetrahydropyran-2-yl)acetic acid and its 2R,6S-trans isomer.

Organic Synthesis with Enzymes. 3. TBADH-Catalyzed Reduction of Chloro Ketones. Total Synthesis of (+)-(S,S)-(cis-6-Methyltetrahydropyran-2-yl)acetic Acid: A Civet Constituent

Highly enantioselective reduction of aliphatic chloro ketones catalyzed by Thermoanaerobium brockii alcohol dehydrogenase (TBADH) afforded the corresponding S chloro alcohols, which are new and useful chiral bifunctional building blocks.The synthetic pote

CONDENSATION OF ENOL SILYL ETHERS WITH 2-ACETOXYTETRAHYDROFURAN AND -TETRAHYDROPYRANS

Trimethylsilyl trifluoromethanesulfonate catalyzes stereoselective condensation of enol silyl ethers and 2-acetoxytetrahydrofuran or -tetrahydropyran derivatives.