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

Base Information

Chemical Name:(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene
CAS No.:291751-48-9
Molecular Formula:C₂₅H₄₀O₄Si
Molecular Weight:432.676
Hs Code.:

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

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

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

There total 9 articles about (+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene 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: 97.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 291751-47-8
(1R,2R,3S,4S,5R)-3α-hydroxy-2β-(p-methoxybenzyloxy)-4β-methyl-8-oxabicyclo[3.2.1]oct-6-en

: 291751-48-9
(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -40 - 0 ℃;
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

: 291751-48-9
(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Guidance literature:: Multi-step reaction with 8 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

7.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

8.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -40 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; (R,R)-N,N-bis-(1-phenylethyl)amine; L-Selectride; 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 / 7.1: Reduction / 8.1: Etherification;
DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 291751-48-9
(+)-(1R,2R,3S,4S,5R)-2β-(p-methoxybenzyloxy)-4β-methyl-3α-(triisopropylsilyloxy)-8-oxabicyclo[3.2.1]oct-6-ene

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: CSA / CH₂Cl₂ / 12 h

2.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -40 - 0 °C

With 2,6-dimethylpyridine; L-Selectride; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Addition / 1.2: Etherification / 2.1: Reduction / 3.1: Etherification;
DOI:10.1002/1099-0690(200006)2000:12<2195::AID-EJOC2195>3.0.CO;2-C