(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

Base Information

Chemical Name:(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate
CAS No.:935264-94-1
Molecular Formula:C₂₄H₃₈O₆Si
Molecular Weight:450.648
Hs Code.:

Synonyms:(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

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Chemical Property of (1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

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Technology Process of (1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

There total 8 articles about (1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate 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: 73.0%

: 935265-05-7
1-{(1R,3R,4R,5S,6R)-4-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl}ethan-1-one

: 935264-94-1
(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In hexane; ethyl acetate; at 20 ℃; for 72h;
DOI:10.1021/jo061456n

Reference yield:

: 935265-01-3
(1S,5R,6R)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

: 935264-94-1
(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / TBHP; VO(acac)2 / benzene; toluene / 2 h / 20 °C

2: NaH / dimethylformamide / 10 h / 20 °C

3: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

4: 18.06 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5: 73 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

With tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; bis(acetylacetonate)oxovanadium; sodium hydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 5: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n

Reference yield:

: 935264-92-9
(1S,2S,3R,4R,6R)-3-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptan-2-ol

: 935264-94-1
(1R,3R,4S,5S,6R)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 10 h / 20 °C

2: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

3: 18.06 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

4: 73 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; water; ethyl acetate; N,N-dimethyl-formamide; 4: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n