(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

Base Information

Chemical Name:(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one
CAS No.:291751-46-7
Molecular Formula:C₁₆H₁₈O₄
Molecular Weight:274.317
Hs Code.:

Synonyms:(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

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Chemical Property of (+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

Chemical Property:

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Technology Process of (+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

There total 6 articles about (+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one 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:

: 545-06-2
trichloroacetonitrile

: 105-13-5
4-Methoxybenzyl alcohol

: (1R,2R,4S,5S)-2-Hydroxy-4-methyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

: 291751-46-7
(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: trichloroacetonitrile; 4-Methoxybenzyl alcohol; With sodium hydride; In diethyl ether; at 0 - 20 ℃; for 2.83333h;

(1R,2R,4S,5S)-2-Hydroxy-4-methyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one; With camphor-10-sulfonic acid; In dichloromethane; for 12h; Further stages.;
DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

Reference yield:

: 40458-77-3
meso-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 291751-46-7
(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: (+)-bis[(R)-1-phenylethyl]amine; LiCl; n-BuLi / tetrahydrofuran; hexane / 3.83 h / -115 - 78 °C

1.2: Et₃N / tetrahydrofuran / -78 °C

2.1: mCPBA / CH₂Cl₂ / 1 h / -35 - -25 °C

2.2: 71 percent / trifluoroacetic acid / CH₂Cl₂ / -25 - 0 °C

3.1: 91 percent / imidazole / dimethylformamide / 12 h / 30 °C

4.1: 91 percent / LDA; TMEDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: HCl / ethanol; H₂O / 12 h / 20 °C

6.1: NaH / diethyl ether / 2.83 h / 0 - 20 °C

6.2: CSA / CH₂Cl₂ / 12 h

With 1H-imidazole; hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; (R,R)-N,N-bis-(1-phenylethyl)amine; sodium hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Isomerization / 1.2: Etherification / 2.1: Oxidation / 2.2: desilylation / 3.1: Etherification / 4.1: Methylation / 5.1: desilylation / 6.1: Addition / 6.2: Etherification;
DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

Reference yield:

: 152139-49-6
(-)-(1R,2R,5R)-2β-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 291751-46-7
(+)-(1R,2R,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 30 °C

2.1: 91 percent / LDA; TMEDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: HCl / ethanol; H₂O / 12 h / 20 °C

4.1: NaH / diethyl ether / 2.83 h / 0 - 20 °C

4.2: CSA / CH₂Cl₂ / 12 h

With 1H-imidazole; hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; hexane; water; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Methylation / 3.1: desilylation / 4.1: Addition / 4.2: Etherification;
DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C