methyl 5(S),6(S)-epoxyeicosatrienoate

Base Information

Chemical Name:methyl 5(S),6(S)-epoxyeicosatrienoate
CAS No.:90080-06-1
Molecular Formula:C₂₁H₃₄O₃
Molecular Weight:334.499
Hs Code.:

Synonyms:

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Chemical Property of methyl 5(S),6(S)-epoxyeicosatrienoate

Chemical Property:

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Technology Process of methyl 5(S),6(S)-epoxyeicosatrienoate

There total 11 articles about methyl 5(S),6(S)-epoxyeicosatrienoate 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:

: 154-17-6
D-2-deoxyglucose

: 90080-06-1
methyl 5(S),6(S)-epoxyeicosatrienoate

Guidance literature:: Multi-step reaction with 11 steps

1: 0.1 percent HCl / 2 h

2: NaIO₄ / methanol; H₂O / 1.5 h / -15 deg C to 0 deg C

3: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 12 h / -78 to 23 deg C

4: H₂ / 5 percent Pd/C / ethanol / 2 h / 760 Torr

5: 1.) 0.4 M HCO₂H, m-chloroperbenzoic acid; 2.) Me₂S / 1.) THF, H₂O, 35 h; 2.) 30 min

6: NaHCO₃ / 10 h / 23 °C

7: 0.5 M HCO₂H / tetrahydrofuran; H₂O / 2.5 h / 65 °C

8: 1.) LiN(SiMe₃)2; 2.) MeOH / 1.) THF, HMPA, -78 to 23 deg C, 12 h; 2.) 2 h, 23 deg C

9: 98 percent / TsOH, 3 A molecular sieves / toluene / 0.5 h / Heating

10: py, DMAP / CH₂Cl₂

11: Et₃N / 12 h

With pyridine; hydrogenchloride; methanol; dmap; sodium periodate; n-butyllithium; formic acid; dimethylsulfide; 3 A molecular sieve; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; toluene;
DOI:10.1021/ja00304a048

Reference yield:

: 105229-01-4,98050-07-8
(2S,3R)-3-Hydroxy-5-methoxy-tetrahydro-furan-2-carbaldehyde

: 90080-06-1
methyl 5(S),6(S)-epoxyeicosatrienoate

Guidance literature:: Multi-step reaction with 9 steps

1: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 12 h / -78 to 23 deg C

2: H₂ / 5 percent Pd/C / ethanol / 2 h / 760 Torr

3: 1.) 0.4 M HCO₂H, m-chloroperbenzoic acid; 2.) Me₂S / 1.) THF, H₂O, 35 h; 2.) 30 min

4: NaHCO₃ / 10 h / 23 °C

5: 0.5 M HCO₂H / tetrahydrofuran; H₂O / 2.5 h / 65 °C

6: 1.) LiN(SiMe₃)2; 2.) MeOH / 1.) THF, HMPA, -78 to 23 deg C, 12 h; 2.) 2 h, 23 deg C

7: 98 percent / TsOH, 3 A molecular sieves / toluene / 0.5 h / Heating

8: py, DMAP / CH₂Cl₂

9: Et₃N / 12 h

With pyridine; methanol; dmap; n-butyllithium; formic acid; dimethylsulfide; 3 A molecular sieve; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; toluene;
DOI:10.1021/ja00304a048

Reference yield:

: (2R,3R)-2-((E)-4,4-Diisopropoxy-but-1-enyl)-5-methoxy-tetrahydro-furan-3-ol

: 90080-06-1
methyl 5(S),6(S)-epoxyeicosatrienoate

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / 5 percent Pd/C / ethanol / 2 h / 760 Torr

2: 1.) 0.4 M HCO₂H, m-chloroperbenzoic acid; 2.) Me₂S / 1.) THF, H₂O, 35 h; 2.) 30 min

3: NaHCO₃ / 10 h / 23 °C

4: 0.5 M HCO₂H / tetrahydrofuran; H₂O / 2.5 h / 65 °C

5: 1.) LiN(SiMe₃)2; 2.) MeOH / 1.) THF, HMPA, -78 to 23 deg C, 12 h; 2.) 2 h, 23 deg C

6: 98 percent / TsOH, 3 A molecular sieves / toluene / 0.5 h / Heating

7: py, DMAP / CH₂Cl₂

8: Et₃N / 12 h

With pyridine; methanol; dmap; formic acid; dimethylsulfide; 3 A molecular sieve; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;
DOI:10.1021/ja00304a048