dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

Base Information

Chemical Name:dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate
CAS No.:156835-34-6
Molecular Formula:C₂₃H₃₀O₈S
Molecular Weight:466.552
Hs Code.:

Synonyms:dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

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Chemical Property of dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

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Technology Process of dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

There total 9 articles about dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate 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:

: 53170-98-2,104411-04-3
(2E)-4-hydroxy-2-methylbut-2-en-1-yl acetate

: 156835-34-6
dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NBS, PPh₃ / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

3: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

4: PPTS / methanol / 12 h / Ambient temperature

5: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

6: 93 percent / dimethylformamide / 24 h / 115 °C

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.786

Reference yield:

: 53170-99-3
(2E)-4-bromo-2-methylbut-2-en-1-yl acetate

: 156835-34-6
dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

3: PPTS / methanol / 12 h / Ambient temperature

4: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

5: 93 percent / dimethylformamide / 24 h / 115 °C

With pyridinium p-toluenesulfonate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.786

Reference yield:

: 54105-78-1
1-[(tetrahydro-2H-pyran-2-yl)oxy]-3-methyl-2-butene

: 156835-34-6
dimethyl (4-acetoxy-3-methyl-2(E)-butenyl)(2-p-toluenesulfonyl-3-butenyl)propanedioate

Guidance literature:: Multi-step reaction with 9 steps

1: 45 percent / selenium dioxide, 70percent aq. t-butyl hydroperoxide / CH₂Cl₂ / 3 h / Ambient temperature

2: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

3: 71 percent / PPTS / methanol / 3 h / Ambient temperature

4: 87 percent / NBS, PPh₃ / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

6: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 2 h

7: PPTS / methanol / 12 h / Ambient temperature

8: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

9: 93 percent / dimethylformamide / 24 h / 115 °C

With tert.-butylhydroperoxide; dmap; N-Bromosuccinimide; selenium(IV) oxide; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.42.786