(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

Base Information

Chemical Name:(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one
CAS No.:367276-82-2
Molecular Formula:C₂₅H₂₆N₂O₃S
Molecular Weight:434.559
Hs Code.:

Synonyms:(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

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Chemical Property of (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

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Technology Process of (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

There total 28 articles about (3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one 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: 90.0%

: 24676-98-0
diethyl 3-methoxycarbonyl-2-propenylidenephosphonate

: 154097-01-5
(3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde

: 367276-82-2
(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: With barium dihydroxide; In 1,4-dioxane; water; at 70 ℃; for 2.5h;
DOI:10.1002/adsc.200404311

Reference yield: 89.0%

: 65866-00-4
(E)-3-methoxycarbonyl-2-propenylidenetriphenylphosphorane

: 154097-01-5
(3aS,4S,6aR)-1,3-dibenzyl-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-carbaldehyde

: 367276-82-2
(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo015730j DOI:10.1016/j.tetlet.2004.08.019

Reference yield:

: 3173-56-6
benzyl isothiocyanate

: 367276-82-2
(3aS,4R,6aR)-1,3-dibenzyl-4-[(1E,3E)-4-methoxycarbonyl-1,3-butanedienyl]-1H-tetrahydrothieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: Multi-step reaction with 18 steps

1.1: aq. NaHCO₃ / dioxane / 20 °C

2.1: pyridine / H₂O / 55 °C

3.1: p-TSA / 20 °C

4.1: NaH / dimethylformamide / 6 h / 0 - 20 °C

5.1: 98 percent / p-TSA / tetrahydrofuran; H₂O / 6 h / Heating

6.1: NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

7.1: Et₃N; DMAP / 1,2-dichloro-ethane / 4 h / Heating

8.1: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -78 - 20 °C

9.1: NaBH₄ / methanol / 4 h / 0 - 20 °C

9.2: 93 percent / TMSCl / 4 h / 40 °C

10.1: NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

11.1: p-TSA / benzene / 6 h / Heating

12.1: 95 percent / Pd-CaCO₃ / methanol / 24 h / 20 °C

13.1: DBU / toluene / 24 h / Heating

14.1: NaBH₄ / ethanol / 2 h / Heating

15.1: 74 percent / Et₃N; DMAP / 4 h / 0 - 20 °C

16.1: 78 percent / Na₂S / dimethylformamide / 2 h / 100 °C

17.1: 82 percent / aq. HCl / acetic acid / 24 h / 20 °C

18.1: 89 percent / CH₂Cl₂ / 12 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium sulfide; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 18.1: Wittig reaction;
DOI:10.1016/j.tetlet.2004.08.019