(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

Base Information

Chemical Name:(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid
CAS No.:183794-47-0
Molecular Formula:C₄₄H₄₉N₅O₇
Molecular Weight:759.902
Hs Code.:

(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

Synonyms:(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

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Chemical Property of (S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

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Technology Process of (S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

There total 25 articles about (S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid 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%

: 183794-46-9
(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester

: 183794-47-0
(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; for 3h;
DOI:10.1021/jo961114p

Reference yield:

: 183794-28-7
{(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol

: 183794-47-0
(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: Multi-step reaction with 12 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: NaH / dimethylsulfoxide / 2 h

9: NaBH₄ / methanol

10: NaI / acetone / Heating

11: 1.) NaHCO₃ / 1.) H₂O, 2.) CH₃CN, room temp., 41 h

12: 100 percent / aq. LiOH / tetrahydrofuran / 3 h

With 2,3,5-trimethyl-pyridine; lithium hydroxide; sodium tetrahydroborate; phosphorus pentachloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile;
DOI:10.1021/jo961114p

Reference yield:

: 183794-29-8
(S)-1-[(3R,5S)-5-(4-Benzyloxy-benzyl)-morpholin-3-yl]-ethane-1,2-diol

: 183794-47-0
(S)-2-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-9-(3-benzyloxycarbonylamino-propyl)-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino]-3-(1H-indol-3-yl)-propionic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent / triethylamine / CH₂Cl₂ / 1.17 h

2: 99 percent / collidine / CH₂Cl₂ / 1.25 h

3: 79 percent / triethylamine / acetonitrile / 10 h / Heating

4: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

5: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

6: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

7: NaH / dimethylsulfoxide / 2 h

8: NaBH₄ / methanol

9: NaI / acetone / Heating

10: 1.) NaHCO₃ / 1.) H₂O, 2.) CH₃CN, room temp., 41 h

11: 100 percent / aq. LiOH / tetrahydrofuran / 3 h

With 2,3,5-trimethyl-pyridine; lithium hydroxide; sodium tetrahydroborate; phosphorus pentachloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile;
DOI:10.1021/jo961114p