((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

Base Information

Chemical Name:((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate
CAS No.:1451079-93-8
Molecular Formula:C₁₆H₁₈O₅
Molecular Weight:290.316
Hs Code.:

Synonyms:((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

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Chemical Property of ((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

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Technology Process of ((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

There total 5 articles about ((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1451079-87-0
(2S)-(5-allyl-4-tert-butyldimethylsilyloxy-3,6-dihydro-2H-pyran-2-yl)methyl benzoate

: 1451079-91-6
((2S,5S)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

: 1451079-93-8
((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

Guidance literature:: (2S)-(5-allyl-4-tert-butyldimethylsilyloxy-3,6-dihydro-2H-pyran-2-yl)methyl benzoate; With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 ℃; for 1h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h; Overall yield = 90 %;
DOI:10.1016/j.tet.2013.07.048

Reference yield:

: 52358-87-9
3-methylenehex-5-en-2-one

: 1451079-93-8
((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: (S)-6,6'-dibromo-1,1'-bi-2-naphthol; titanium(IV) isopropylate / toluene / 5.08 h / 0 - 20 °C

3.1: lithium aluminium tetrahydride / diethyl ether / 0.17 h / 0 °C

4.1: triethylamine; dmap / dichloromethane / 24 h / 0 - 20 °C

5.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 1 h / 0 °C

5.2: 0.25 h / 0 °C

With titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; potassium tert-butylate; (S)-6,6'-dibromo-1,1'-bi-2-naphthol; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/j.tet.2013.07.048

Reference yield:

: 1451079-76-7
2-tert-butyldimethylsilyloxy-3-methylenehexa-1,5-diene

: 1451079-93-8
((2S,5R)-5-allyl-5-hydroxy-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: (S)-6,6'-dibromo-1,1'-bi-2-naphthol; titanium(IV) isopropylate / toluene / 5.08 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 0.17 h / 0 °C

3.1: triethylamine; dmap / dichloromethane / 24 h / 0 - 20 °C

4.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 1 h / 0 °C

4.2: 0.25 h / 0 °C

With titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; (S)-6,6'-dibromo-1,1'-bi-2-naphthol; triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/j.tet.2013.07.048