(2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one

Base Information

• Chemical Name: (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one
• CAS No.: 183794-41-4
• Molecular Formula: C₂₃H₃₈ClN₃O₅SSi
• Molecular Weight: 532.176

Synonyms:(2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one

Chemical Property of (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one

Chemical Property:

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Technology Process of (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one

There total 17 articles about (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-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: 100.0%

(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one (183794-40-3) → (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one (183794-41-4)

Guidance literature:

With hydrogen; acetic acid; palladium; In methanol; ethanol; water; for 48h;

DOI:10.1021/jo961114p

Reference yield:

N2-(tert-butoxycarbonyl)-L-ornithine (21887-64-9) → (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one (183794-41-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Me₄NOH / 1.) MeOH, EtOH, 2.) DMF, 3 h

2: 93 percent / SOCl₂ / 23 h / Ambient temperature

3: 84 percent / triethylamine / dimethylformamide / 2.5 h / 0 °C

4: 97 percent / aq. LiOH / tetrahydrofuran / 2.5 h / Ambient temperature

5: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

6: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

7: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 57 percent / NaH / dimethylsulfoxide / 2 h

9: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

With lithium hydroxide; thionyl chloride; phosphorus pentachloride; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo961114p

Reference yield:

{(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol (183794-28-7) → (2S,6R,7S,9S)-9-(3-Amino-propyl)-6-chloro-2-(4-hydroxy-benzyl)-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one (183794-41-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / dioxane / 9 h / Heating

2: 80 percent / triethylamine / CH₂Cl₂ / 1.17 h

3: 99 percent / collidine / CH₂Cl₂ / 1.25 h

4: 79 percent / triethylamine / acetonitrile / 10 h / Heating

5: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

6: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

7: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 57 percent / NaH / dimethylsulfoxide / 2 h

9: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

With 2,3,5-trimethyl-pyridine; phosphorus pentachloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; triethylamine; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jo961114p

upstream raw materials:

(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undecan-10-one

N₂-(tert-butoxycarbonyl)-L-ornithine

{(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol

(S)-1-[(3R,5S)-5-(4-Benzyloxy-benzyl)-morpholin-3-yl]-ethane-1,2-diol

Downstream raw materials:

{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

{3-[(2S,6R,7S,9S)-6-Chloro-2-(4-hydroxy-benzyl)-10-oxo-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

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