105814-63-9

Upstream product

• 598-32-3 2-hydroxy-3-butene 
• 144-48-9 iodacetamide 
• 34495-74-4 Ethyl 4-hexenoate 
• 41143-12-8 hex-4-ynoic acid 
• 6089-09-4 4-pentynoic acid 
• 124558-70-9 (S)-4-Ethylsulfanyl-5-((S)-1-hydroxy-ethyl)-5H-furan-2-one 
• 1577-20-4 (E)-hex-4-enoic acid 

Downstream Products

• 89158-15-6 p-nitrobenzoate of L-(+)-rhodinono-γ-lactone 
• 89158-14-5 p-nitrobenzoate of D-(+)-amicetono-γ-lactone 
• 876152-53-3 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol 
• 130258-63-8 (3R,5R)-5-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-dihydro-furan-2-one 
• 130258-63-8 (3S,5R)-5-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-dihydro-furan-2-one 
• 130323-45-4 (R)-5-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-dihydro-furan-2-one 
• 54656-51-8 (R)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one 
• 876152-44-2 tert-Butyl-[2-((2S,3R,6S)-6-{(E)-(S)-3-[(2S,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethoxy]-diphenyl-silane 
• 876152-52-2 tert-Butyl-[2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethoxy]-diphenyl-silane 
• 876152-35-1 tert-Butyl-((2R,3R,6S)-6-{(E)-(S)-3-[(2S,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane 
• 876152-50-0 tert-Butyl-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane 
• 876152-48-6 (S)-1-((2R,4S)-4-Methyl-5-phenylsulfanyl-tetrahydro-furan-2-yl)-ethanol 
• 876152-41-9 (3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-2-phenylsulfanyl-tetrahydro-furan 
• 876152-40-8 (S)-1-((R)-5-oxotetrahydrofuran-2-yl)ethyl 4-nitrobenzoate 

Relevant academic research and scientific papers

Synthesis of the C14-C28 fragment of tetronasin

A synthesis of the C14-C28 fragment of Tetronasin features an S E2 reaction between a cationic η3-allylmolybdenum complex and and an α-metallated tetrahydrofuran. Georg Thieme Verlag Stuttgart.

Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: Facile synthesis of γ-lactones

Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis 4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.

(+/-)-erythro-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes

Reaction of β-ethylthio-β-lithioacrylate 1A with α-chloroaldehydes furnished predominantly the erythro products 3, which were isolated as γ-lactones 4.At room temperature intermediates 3 are transformed into the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones 8.Raney nickel treatment provided interesting natural γ-lactone derivatives; thus, from erythro-8c the socalled L-factor erythro-9c was obtained.Similarly, from β-methoxy β-lithioacrylate 10A the (+/-)-erythro-γ,δ-dihydroxycarboxylic acid δ-lactone erythro-11 was gained.

A Simple, General Diastereoselective Synthesis of 5-Hydroxyalkylbutan-4-olides

cis- and trans-Hex-4-enoic acids and their 6-n-propyl and n-butyl derivatives, when treated with a 1.1 molar excess of m-chloroperbenzoic acid and Amberlyst-15 as catalyst in CH2Cl2 at 20 deg C, gave the corresponding threo- and erythro-5-hydroxyalkylbutan-4-olides in quantitative yields.