334972-54-2

Upstream product

• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 334972-53-1 (S)-1-((tert-butyldimethylsilyl)oxy)hex-5-en-2-ol 
• 127102-61-8 (S)-hex-5-ene-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 764-59-0 hex-5-en-1-al 

Downstream Products

• 334706-33-1 Benzoic acid (E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-hex-2-enyl ester 
• 934545-49-0 (S)-2-((4-methoxybenzyl)oxy)hex-5-en-1-ol 
• 442913-72-6 (S)-2-((4-methoxybenzyl)oxy)hex-5-enoic acid 
• 334972-61-1 (1S,2R,5R)-2-[(2'R,5'Z)-5'-(2''-Phenylsulfonylethylidene)-tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane 
• 350485-98-2 (1S,2R,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-1-(tert-butyldimethylsilyloxy)-5-(1-methylethenyl)cyclopentane 
• 334972-46-2 Ethyl (R)-2-[(2'R,5'S)-5'-(4-methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enoate 
• 334972-59-7 Ethyl (R)-2-[(2'S,5'S)-5'-(4-methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enoate 
• 334972-58-6 Ethyl (S)-2-[(2'R,5'S)-5'-(4-methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enoate 
• 334972-60-0 Ethyl (S)-2-[(2'S,5'S)-5'-(4-methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enoate 
• 334972-48-4 (1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol 
• 334972-47-3 (R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal 
• 334972-55-3 (2RS,5S)-6-(tert-Butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)hexane-1,2-diol 
• 334972-43-9 (S)-5-(tert-Butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)pentanal 

Relevant academic research and scientific papers

Formal synthesis of pinolide via l-proline-catalyzed sequential α-aminooxylation, Horner-Wadsworth-Emmons olefination and Sharpless asymmetric dihydroxylation

A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of l-proline catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule.

Synthesis of complex allylic esters via C-H oxidation vs C-C Bond formation

A highly general, predictably selective C-H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (16 examples, E/Z ≤ 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C-H oxidation vs C-C bond-forming methods are evaluated and discussed in four case studies.

Triterpenoid total synthesis. Part 6. Synthesis of testudinariols A and B, triterpene metabolites of the marine mollusc Pleurobrancus testudinarius

Testudinariols A (1) and B (1′) are ichthyotoxic and structurally unusual triterpene alcohols isolated from the skin and the mucus of the marine mollusc Pleurobrancus testudinarius. The first synthesis of (+)-1 and (+)-1′ was achieved by starting from (R)-glycidol.

Synthesis of (+)-testudinariol A, a triterpene metabolite of the marine mollusc Pleurobrancus testudinarius

Testudinariol A (1) is an ichthyotoxic and structurally unusual triterpene alcohol isolated from the skin and the mucus of the marine mollusc Pleurobrancus testudinarius. A stereoselective synthesis of (+)-1 was achieved by starting from (R)-glycidol.