(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

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 methyl ester
CAS No.:183794-46-9
Molecular Formula:C₄₅H₅₁N₅O₇
Molecular Weight:773.929
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 methyl ester

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 methyl ester

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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 methyl ester

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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 methyl ester

There total 24 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 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:

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

: 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

Guidance literature:: Multi-step reaction with 10 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

With 2,3,5-trimethyl-pyridine; 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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 11 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

With 2,3,5-trimethyl-pyridine; 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:

: 183794-32-3
(2S,6R,7R)-2-(4-Benzyloxy-benzyl)-7-(tert-butyl-dimethyl-silanyloxy)-4-oxa-1-aza-bicyclo[4.2.0]octane

: 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

Guidance literature:: Multi-step reaction with 7 steps

1: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

2: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

3: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

4: NaH / dimethylsulfoxide / 2 h

5: NaBH₄ / methanol

6: NaI / acetone / Heating

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

With sodium tetrahydroborate; phosphorus pentachloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1021/jo961114p