63357-98-2

Upstream product

• 4762-26-9 hexyltriphenylphosphonium bromide 
• 134359-16-3 γ-(prop-2-enyl)-γ-butyrolactone 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 1968-40-7 ethyl 4-pentenoate 
• 73697-60-6 ethyl 3-(oxiran-2-yl)propanoate 
• 5711-29-5 <9,10-2H2>-oleic acid 

Downstream Products

• 127251-21-2 Benzoic acid (4Z,7Z)-(R)-11-methoxycarbonyl-1-((Z)-oct-2-enyl)-undeca-4,7-dienyl ester 
• 117346-20-0 12(R)-Hydroxy-5,8,14-(Z,Z,Z)-eicosatrienoic acid 
• 122221-81-2 Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester 
• 122221-80-1 Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester 
• 122221-84-5 Benzoic acid (2E,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester 
• 122221-82-3 Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester 
• 122221-78-7 [(2E,8Z)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,8-dienyl]-triphenyl-phosphonium 
• 122221-83-4 C₃₅H₄₄O₆ 
• 122221-77-6 (2E,8Z)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,8-dienoic acid methyl ester 
• 127251-17-6 [(Z)-(S)-1-((E)-5-Bromo-pent-3-enyl)-non-3-enyloxy]-tert-butyl-diphenyl-silane 

Relevant academic research and scientific papers

METHOD FOR SYNTHESIZING A PRECURSOR OF A SINGLE DAIRY-LACTONE ISOMER

This disclosure provides a method for preparing a precursor of a single dairy-lactone isomer, methods of preparing a single dairy-lactone isomer, and to the organoleptic uses thereof.

Chemo-enzymatic synthesis of chiral epoxides ethyl and methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable levoglucosenone: An access to enantiopure (S)-dairy lactone

Chiral epoxides-such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)-are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%-50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO.

Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus

Addition of [9,10-2H2]oleic acid to cultures of the yeast Sporobolomyces odorus led to the formation of labeled (R)-γ-decanolactone and both enantiomers of (Z)-6-γ-dodecenolactone and γ-dodecanolactone. The labeling patterns of these lactones were estimated by a quantitative gas chromatography/mass spectrometry method, suitable for ring-labeled lactones. For the first time, there is strong evidence of oleic acid being a genuine precursor of the important aroma compound (R)-γ-decanolactone. On the basis of the presented and former results, a new biosynthetic pathway of this compound is proposed. Starting with a strict enantioselective (R)-12-hydroxylation of oleic acid as an initial step, the following β-oxidation led to the lactone. In addition, biosynthetic aspects of the formation of (Z)-6-γ-dodecenolactone and γ-dodecanolactone in S. odorus are discussed.

TOTAL SYNTHESIS OF 5(S),12(S)- AND 5(S),12(R)-DIHYDROXYEICOSA-6(Z),8(E),14(Z)-TRIENOIC ACIDS, METABOLITES OF LEUKOTRIENE B4

The recently identified dihydro-leukotriene B4 metabolite 1 and its C(12)-epi analogue 2 were prepared by Wittig coupling of segments derived from 2-deoxy-D-ribose and L-glutamic acid.

Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa)

Six unsaturated γ-lactones, (Z)-5-octen-4-olide (1), (Z)-5-decen-4-olide (2), (Z)-6-nonen-4-olide (3), (Z)-6-dodecen-4-olide (4), (Z,Z)-6,9-dodecadien-4-olide (5), and tuberolide (6) have been identified for the first time in tuberose absolute (from Polianthes tuberosa L.).All structures were corroborated by synthesis and all, except 3 and 4, are new.An improved method for the stereoselective synthesis of (+/-)-cis-bicyclo-non-3-en-7-one (23) by an AlCl3-catalyzed Diels-Alder reaction is reported.

Vinyl-copper derivatives-XI1 1 Part X: A. Alexakis, G. Cahiez and J.F. Normant, Synthesis, 826 (1979). Reactivity of Z-alkenyl cuprates towards various electrophiles. Application to the synthesis of some natural products

Z-Alkenylcuprates 1 and 2, prepared in situ by addition of acetylene to alkylcuprates, react with a variety of electrophiles (epoxides, carbon dioxide, aldehydes) and give conjugate addition products with α,β-unsaturated aldehydes, ketones and esters, and with activated cyclopropanes. They also add across the triple bond of some alkynes. The synthesis of natural products (7,9,22) is described.