(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

Base Information

Chemical Name:(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one
CAS No.:866467-75-6
Molecular Formula:C₂₀H₂₂N₂O₂S
Molecular Weight:354.473
Hs Code.:

Synonyms:(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

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Chemical Property of (3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

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Technology Process of (3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

There total 10 articles about (3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[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: 75.0%

: 866467-74-5
(3aS,4S,6aR)-1,3-dibenzyl-4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

: 866467-75-6
(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2005.07.070

Reference yield:

: 112878-92-9
(3S,7aR)-6-benzyl-3-phenyldihydro-3H,5H-imidazo[1,5-c]thiazole-5,7(6H)-dione

: 866467-75-6
(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / sodium borohydride / methanol / 0 - 20 °C

2.1: 99 percent / p-TSA / methanol / 0.17 h / 20 °C

3.1: tri-n-butyltin hydride; AIBN / benzene / 0.5 h / Heating

3.2: 80 percent / anhydrous potassium carbonate / acetone / 20 °C

4.1: 93 percent / p-TSA / 0.08 h / 0 °C

5.1: 78 percent / DIBAL-H / toluene / 2 h / -78 °C

6.1: 80 percent / DBU / CH₂Cl₂ / 0.5 h / Heating

7.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating

8.1: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; toluene; benzene;
DOI:10.1016/j.tet.2005.07.070

Reference yield:

: 866467-71-2
(3S,7aR)-6-benzyl-7-methoxy-3-phenyltetrahydro-5H-imidazo[1,5-c][1,3]thiazol-5-one

: 866467-75-6
(3aS,4S,6aR)-1,3-dibenzyl-4-(hydroxymethyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tri-n-butyltin hydride; AIBN / benzene / 0.5 h / Heating

1.2: 80 percent / anhydrous potassium carbonate / acetone / 20 °C

2.1: 93 percent / p-TSA / 0.08 h / 0 °C

3.1: 78 percent / DIBAL-H / toluene / 2 h / -78 °C

4.1: 80 percent / DBU / CH₂Cl₂ / 0.5 h / Heating

5.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating

6.1: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; benzene;
DOI:10.1016/j.tet.2005.07.070