(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

Base Information

Chemical Name:(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone
CAS No.:167824-09-1
Molecular Formula:C₃₅H₃₂N₄O₂
Molecular Weight:540.665
Hs Code.:

Synonyms:(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

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Chemical Property of (4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

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Technology Process of (4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

There total 16 articles about (4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone 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:

: 2448-45-5
Cbz-D-Phe

: 167824-09-1
(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

Guidance literature:: Multi-step reaction with 13 steps

1: N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C

2: tetrahydrofuran; dimethylformamide / 0.5 h

3: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

4: CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

5: diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) CuCN / 1.) THF, a) -70 deg C, 20 min, b) 0 deg C, 30 min, 2.) THF, -70 deg C, 60 min

7: MCPBA / CH₂Cl₂ / 7 h / 0 °C

8: NaN₃, NH₄Cl / dimethylformamide; H₂O / a) 85 deg C, 3 h, b) RT, overnight

9: 90 percent / diisopropylamine / CH₂Cl₂ / Heating

10: H₂, AcOH / Pearlman's catalyst / ethyl acetate / 20 h / 2844.3 Torr

11: tetrahydrofuran / Ambient temperature

12: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 45 min

13: 4 N HCl / methanol; dioxane / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; sodium hydride; ammonium chloride; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm970081i

Reference yield:

: 41518-17-6
C₂₂H₂₅NO₆

: 167824-09-1
(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

Guidance literature:: Multi-step reaction with 12 steps

1: tetrahydrofuran; dimethylformamide / 0.5 h

2: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

4: diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 1.) CuCN / 1.) THF, a) -70 deg C, 20 min, b) 0 deg C, 30 min, 2.) THF, -70 deg C, 60 min

6: MCPBA / CH₂Cl₂ / 7 h / 0 °C

7: NaN₃, NH₄Cl / dimethylformamide; H₂O / a) 85 deg C, 3 h, b) RT, overnight

8: 90 percent / diisopropylamine / CH₂Cl₂ / Heating

9: H₂, AcOH / Pearlman's catalyst / ethyl acetate / 20 h / 2844.3 Torr

10: tetrahydrofuran / Ambient temperature

11: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 45 min

12: 4 N HCl / methanol; dioxane / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; sodium hydride; ammonium chloride; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm970081i

Reference yield:

: 120452-49-5
N-methoxy-N-methyl-(R)-N²-Cbz-phenylalaninamide

: 167824-09-1
(4R,5R,6R)-tetrahydro-1,3-bis[(3-cyanophenyl)methyl]-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

Guidance literature:: Multi-step reaction with 11 steps

1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2: CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

3: diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 1.) CuCN / 1.) THF, a) -70 deg C, 20 min, b) 0 deg C, 30 min, 2.) THF, -70 deg C, 60 min

5: MCPBA / CH₂Cl₂ / 7 h / 0 °C

6: NaN₃, NH₄Cl / dimethylformamide; H₂O / a) 85 deg C, 3 h, b) RT, overnight

7: 90 percent / diisopropylamine / CH₂Cl₂ / Heating

8: H₂, AcOH / Pearlman's catalyst / ethyl acetate / 20 h / 2844.3 Torr

9: tetrahydrofuran / Ambient temperature

10: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 45 min

11: 4 N HCl / methanol; dioxane / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; sodium hydride; ammonium chloride; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm970081i