{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

Base Information

Chemical Name:{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
CAS No.:183794-42-5
Molecular Formula:C₃₁H₄₄ClN₃O₇SSi
Molecular Weight:666.311
Hs Code.:

{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

Synonyms:{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

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Chemical Property of {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

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Technology Process of {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

There total 20 articles about {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 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: 87.0%

: 75315-63-8
N-(benzyloxycarbonyl)succinimide

: 183794-41-4
(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

: 183794-42-5
{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

: Carbonic acid benzyl ester 4-[(2S,6R,7S,9S)-9-(3-benzyloxycarbonylamino-propyl)-6-chloro-10-oxo-8-(2-trimethylsilanyl-ethanesulfonyl)-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-2-ylmethyl]-phenyl ester

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; water; for 18h;
DOI:10.1021/jo961114p

Reference yield:

: 21887-64-9
N₂-(tert-butoxycarbonyl)-L-ornithine

: 183794-42-5
{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

Guidance literature:: Multi-step reaction with 10 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

10: 87 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

With lithium hydroxide; thionyl chloride; phosphorus pentachloride; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo961114p

Reference yield:

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

: 183794-42-5
{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

Guidance literature:: Multi-step reaction with 9 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: 57 percent / NaH / dimethylsulfoxide / 2 h

8: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

9: 87 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

With 2,3,5-trimethyl-pyridine; phosphorus pentachloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo961114p