106758-72-9

Upstream product

• 99892-72-5 (1R,2S)-2-Hydroxy-1-methyl-cyclohexanecarbaldehyde 
• 106680-71-1 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-(2-hydroxymethyl-2-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol 
• 106680-71-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-(2-hydroxymethyl-2-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol 
• 106680-70-0 (1R,2S)-1-Methyl-2-((2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanecarbaldehyde 
• 99892-70-3 (1R,2S)-1-Methyl-2-((2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-3-enecarbaldehyde 
• 155907-01-0 (1S,6S)-6-(hydroxymethyl)-6-methyl-2-cyclohexenol 
• 137037-08-2 (1R,2S)-2-acetoxy-1-methyl-3-cyclohexenecarbaldehyde 
• 66088-37-7 ethyl 1-methyl-2-oxocyclohexancarboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Downstream Products

• 99646-08-9 t-2-(1-hydroxy-1-methylethyl)-2-methylcyclohexan-r-1-ol 
• 186038-23-3 (1R,2R)-2-Hydroxy-1-methyl-cyclohexanecarbaldehyde 

Relevant academic research and scientific papers

Designed Chiral Acyl Radical Equivalents. Preparation and Cyclizations of Disymmetrically Substituted 1,3-Dioxabicyclo[4.4.0]decan-2-yl Radicals

The diastereoselectivity of 5-exo-trigonal cyclizations of 2-(4-penten-1-yl)-1,3-dioxolan-2-yl and 2-(4- penten-1-yl)-1,3-dioxan-2-yl radicals is investigated. When dioxolanes or dioxanes derived from C2 symmetrically substituted diols are employed the diastereoselectivity is poor. In the dioxanyl series this is a consequence of the cyclization occurring through a twist-boat conformer. Disymmetrically substituted dioxanyl radicals, derived from the alcohols 21 and 41, are, however, constrained to chairlike conformations and accordingly give rise to highly diastereoselective cyclizations. Conditions are described for the hydrolysis of the resulting spiroacetals and for determination of the ee of the resulting 2-methylcyclopentanones.

Asymmetric catalysis of Diels-Alder cycloadditions by an MS-free binaphthol-titanium complex: Dramatic effect of MS, linear vs positive nonlinear relationship, and synthetic applications

Asymmetric Diets-Aider (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20°C. Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (±)-1.

STEREOCHEMICAL VARIATIONS IN AQUEOUS CYCLOADDITIONS USING GLYCO-ORGANIC SUBSTRATES AS A CONSEQUENCE OF CHEMICAL MANIPULATIONS ON THE SUGAR MOIETY

Chemical modifications of the sugar moiety in dienyl glycosides allowed us to rationalize the stereochemistry of our aqueous cycloadditions using glyco-organic substrates.In this way, several dienyl glucosides having benzyl group in 2 or 6 position of the

GLYCO-ORGANIC SUBSTRATES IN ORGANIC SYNTHESIS. PREPARATION OF A WATER SOLUBLE BUTADIENYL-ETHER AND ITS USE IN AQUEOUS CYCLOADDITION.

A chiral water-soluble butadienyl-ether containing free glucose as hydrophilic moiety was synthesized and used in aqueous cycloaddition reaction with methacrolein to afford through pure endo transition state, only two diastereoisomers from which the sugar