methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

Base Information

Chemical Name:methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate
CAS No.:476003-41-5
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

Synonyms:methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

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Chemical Property of methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

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Technology Process of methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

There total 11 articles about methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate 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: 83.0%

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: (2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-benzyl]-2-methyl-oxirane-2-carbaldehyde

: 476003-41-5
methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

Guidance literature:: In dichloromethane; at 0 - 20 ℃;
DOI:10.1271/bbb.66.1915

Reference yield:

: 57433-93-9
hydroquinone monomethoxymethyl ether

: 476003-41-5
methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / K₂CO₃ / acetone / 10 h / Heating

2: 88 percent / N,N-diethylaniline / 5 h / 220 °C

3: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

4: 98 percent / 4-methylmorpholine-4-oxide; aq. OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

5: NaIO₄ / methanol; H₂O / 1 h / 20 °C

6: 98 percent / CH₂Cl₂ / 0 - 20 °C

7: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 - 20 °C

8: D-(-)-diethyl tartrate; tert-butylhydroperoxide; titanium tetraisopropoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

9: oxalyl chloride; DMSO / CH₂Cl₂ / 1.25 h / -78 - -45 °C

10: 83 percent / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N,N-diethylaniline; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 6: Wittig reaction / 8: Sharpless epoxydation / 9: Swern oxidation / 10: Wittig olefination;
DOI:10.1271/bbb.66.1915

Reference yield:

: 123-31-9,8027-02-9
hydroquinone

: 476003-41-5
methyl (2E,4S,5S)-6-[2-(tert-butyldimethylsilyloxy)-5-(methoxymethoxy)phenyl]-4-methyl-4,5-epoxy-2-hexenoate

Guidance literature:: Multi-step reaction with 11 steps

1: 65 percent / N,N-diisopropylethylamine / acetonitrile / 0 - 20 °C

2: 85 percent / K₂CO₃ / acetone / 10 h / Heating

3: 88 percent / N,N-diethylaniline / 5 h / 220 °C

4: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

5: 98 percent / 4-methylmorpholine-4-oxide; aq. OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

6: NaIO₄ / methanol; H₂O / 1 h / 20 °C

7: 98 percent / CH₂Cl₂ / 0 - 20 °C

8: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 - 20 °C

9: D-(-)-diethyl tartrate; tert-butylhydroperoxide; titanium tetraisopropoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

10: oxalyl chloride; DMSO / CH₂Cl₂ / 1.25 h / -78 - -45 °C

11: 83 percent / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; N,N-diethylaniline; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 7: Wittig reaction / 9: Sharpless epoxydation / 10: Swern oxidation / 11: Wittig olefination;
DOI:10.1271/bbb.66.1915