73440-88-7

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 100-44-7 benzyl chloride 
• 59599-25-6 (1R)-(-)-cis-3-hydroxyisoborneol 
• 100-52-7 benzaldehyde 
• 88969-71-5 (1S,2R,6S,7R)-1,10,10-Trimethyl-4-phenyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane 
• 88969-71-5 dioxa-3,5 exo phenyl-4 syn trimethyl-7,10,10 tricyclo <5.2.1.0^2,6> decane 
• 13837-85-9 1,7,7-trimethylbicyclo[2.2.1]heptane-exo,exo-2,3-diol 

Downstream Products

• 80868-48-0 cis-3-benzyloxyisobornyl acrylate 
• 80868-57-1 Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,3R,4S)-3-benzyloxy-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104128-80-5 C₄₄H₆₄O₈ 
• 104128-63-4 (1R,3S,4S)-3-Benzyloxy-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 104128-81-6 (-)-(1R,4S,4aS,9S,10S,14aS,15S,18R,18aR,22aR)-eicosahydro-4,15,23,23,24,24-hexamethyl-9,10-bis-(tosyloxymethyl)-1,4:15,18-dimethanodibenzo<1,4,7,10,13,16>hexaoxacyclooctadecin 
• 73440-86-5 (1R,2S,3R,4S)-1,2-bis-<2-(2'-tosyloxy)ethoxy-1,7,7-trimethylbicyclo<2.2.1>hept-3-yloxy>-ethane 
• 104128-82-7 C₄₄H₆₀O₈S₂ 
• 104154-99-6 (1R,3R,4S)-3-benzyloxy-1,7,7-trimethylbicyclo<2.2.1>hept-2-one 

Relevant academic research and scientific papers

Biomimetic Studies Using Artificial Systems. II. Enantioselective Thiolysis of D- or L-α-Amino Acid Ester Salts by Thiol-Bearing Chiral Crown Ethers as an Enzyme Model

The rates of transacylation were studied between thiol-bearing chiral crown ethers (1-10) and α-amino acid p-nitrophenyl ester salts.Enantioselectivities, kD/kL ratios, of 6.5 for valine ester salt, 8.7 for phenylalanine ester salt, and 7.7 for valine ester salt were achieved by 1, 5, and 8, respectively.Saturation phenomena of rate acceleration depending on crown concentration were observed and analysis of these data revealed that the chiral recognition occurs in the step of liberation of p-nitrophenol by intra-complex thiolysis, not in the complex-forming step.A possible mechanism for the anantioselectivity is proposed on the basis of the kinetic data.Keywords - crown ether; transacylation; pseudo-first-order rate constant; enantioselectivity; thiolysis; intra-complex reaction; enzyme model

A FACILE CLEAVAGE OF BENZYLIDENE ACETALS WITH DIISOBUTYLALUMINUM HYDRIDE

Benzylidene acetals of 1,2- and 1,3-glycols are easily cleft by diisobutylaluminum hydride in a toluene solution at 0 deg C - room temperature to give the corresponding monobenzyl ethers of the glycols.In general the reaction proceeds excellently in regioselective manner depending on the stereochemical environment.

Asymmetric Induction in Diels-Alder Reactions to Acrylates Derived from Chiral sec-Alcohols

Starting from the enantiomerically pure monoterpenes (+)-pulegone (3), (+)-limonene (7), (-)-β-pinene (9), (+)- and (-)-camphor (13) or (+)-cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 and 18 were prepared; their acrylates II underwent a TiCl4-promoted Diels-Alder addition to cyclopentadiene (Scheme 3, Table) giving in a predictable manner either the (2R)- or the (2S)-adducts III with 63 to 88percent asymmetric induction.