(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester
CAS No.:699536-20-4
Molecular Formula:C₃₁H₄₂N₄O₇
Molecular Weight:582.697
Hs Code.:

Synonyms:(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

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Chemical Property of (S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

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Technology Process of (S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

There total 15 articles about (S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester 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:

: 5545-54-0
N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine

: 699536-20-4
(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: N-methylmorpholine; isobutyl chloroformate / CH₂Cl₂ / 0.25 h / -20 °C

1.2: 85 percent / CH₂Cl₂ / 3 h / 20 °C

2.1: 80 percent / tetrahydrofuran / 4 h / -78 °C

3.1: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C

4.1: 75 percent / KOH / H₂O; ethanol / 5 h / Heating

5.1: 85 percent / 4-(dimethylamino)pyridine; CuSO₄; triflyl azide / CH₂Cl₂ / 2 h

6.1: NaOH; NBu₄HSO₄ / benzene; H₂O / 1 h

7.1: 0.88 g / N-methylmorpholine oxide; OsO₄ / H₂O; acetone; tetrahydrofuran / 10 h

8.1: 85 percent / Na₂CO₃; Pb(OAc)4 / benzene / 3 h / 20 °C

9.1: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h

10.1: 85 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tertramethyluronium*PF₆; diisopropylethylamine / dimethylformamide / 15 h / 20 °C

11.1: 99 percent / formic acid / 20 h / 20 °C

12.1: N,N'-dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C

13.1: 0.12 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / dioxane / 12 h / Heating

14.1: 0.04 g / SnCl₄; triethylamine; thiophenol / 2 h / 20 °C

With 4-methyl-morpholine; lead(IV) acetate; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; formic acid; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; tin(IV) chloride; sodium tris(acetoxy)borohydride; sodium carbonate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; thiophenol; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo0356863

Reference yield:

: 699536-17-9
benzyl [(S)-2-(4-tert-butoxyphenyl)-1-(methoxy(methyl)carbamoyl)ethyl]carbamate

: 699536-20-4
(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 80 percent / tetrahydrofuran / 4 h / -78 °C

2: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C

3: 75 percent / KOH / H₂O; ethanol / 5 h / Heating

4: 85 percent / 4-(dimethylamino)pyridine; CuSO₄; triflyl azide / CH₂Cl₂ / 2 h

5: NaOH; NBu₄HSO₄ / benzene; H₂O / 1 h

6: 0.88 g / N-methylmorpholine oxide; OsO₄ / H₂O; acetone; tetrahydrofuran / 10 h

7: 85 percent / Na₂CO₃; Pb(OAc)4 / benzene / 3 h / 20 °C

8: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h

9: 85 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tertramethyluronium*PF₆; diisopropylethylamine / dimethylformamide / 15 h / 20 °C

10: 99 percent / formic acid / 20 h / 20 °C

11: N,N'-dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C

12: 0.12 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / dioxane / 12 h / Heating

13: 0.04 g / SnCl₄; triethylamine; thiophenol / 2 h / 20 °C

With lead(IV) acetate; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; formic acid; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; tin(IV) chloride; sodium tris(acetoxy)borohydride; sodium carbonate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; thiophenol; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo0356863

Reference yield:

: 699536-18-0
benzyl [(S)-1-(4-tert-butoxybenzyl)-2-oxopent-4-enyl]carbamate

: 699536-20-4
(S)-2-((S)-2-{(S)-10-[(S)-1-Amino-2-(4-hydroxy-phenyl)-ethyl]-3,6-dioxo-[1,4,7]oxadiazecan-7-yl}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 14 percent / K-Selectride / tetrahydrofuran / 4 h / -78 °C

2: 75 percent / KOH / H₂O; ethanol / 5 h / Heating

3: 85 percent / 4-(dimethylamino)pyridine; CuSO₄; triflyl azide / CH₂Cl₂ / 2 h

4: NaOH; NBu₄HSO₄ / benzene; H₂O / 1 h

5: 0.88 g / N-methylmorpholine oxide; OsO₄ / H₂O; acetone; tetrahydrofuran / 10 h

6: 85 percent / Na₂CO₃; Pb(OAc)4 / benzene / 3 h / 20 °C

7: 82 percent / triethylamine; NaBH(OAc)3 / 1,2-dichloro-ethane / 45 h

8: 85 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tertramethyluronium*PF₆; diisopropylethylamine / dimethylformamide / 15 h / 20 °C

9: 99 percent / formic acid / 20 h / 20 °C

10: N,N'-dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C

11: 0.12 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / dioxane / 12 h / Heating

12: 0.04 g / SnCl₄; triethylamine; thiophenol / 2 h / 20 °C

With lead(IV) acetate; dmap; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; formic acid; triflic azide; tetra(n-butyl)ammonium hydrogensulfate; tin(IV) chloride; sodium tris(acetoxy)borohydride; sodium carbonate; potassium tri-sec-butyl-borohydride; copper(II) sulfate; thiophenol; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo0356863