[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester
CAS No.:494836-49-6
Molecular Formula:C₃₅H₃₉N₇O₅
Molecular Weight:637.739
Hs Code.:

[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

Synonyms:[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

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Chemical Property of [(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

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Technology Process of [(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

There total 14 articles about [(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-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: 65.0%

: 147291-50-7,854762-31-5
benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate

: 494836-36-1
(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carboxylic acid

: 494836-49-6
[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(02)00612-1

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 494836-49-6
[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: LiHMDS / tetrahydrofuran / -78 °C

1.2: 92 percent / tetrahydrofuran / -78 °C

2.1: Dibal-H / toluene / -78 °C

3.1: Et₃N; DMAP / CH₂Cl₂

4.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

5.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 760 Torr

6.1: B-bromocatecholborane / CH₂Cl₂

7.1: toluene / Heating

8.1: 80 percent / KH / tetrahydrofuran

9.1: n-BuLi / tetrahydrofuran / -78 °C

9.2: 78 percent / tetrahydrofuran / -78 °C

10.1: t-BuLi / tetrahydrofuran / -78 °C

10.2: 60 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

11.1: 76 percent / TBAF / tetrahydrofuran

12.1: TPAP; NMO / CH₂Cl₂

13.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

14.1: 65 percent / EDC; HOBt; i-Pr₂NEt / dimethylformamide

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; bromocatecholborane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0960-894X(02)00612-1

Reference yield:

: 494836-25-8
5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 494836-49-6
[(4-{[((1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-1-ethyl-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: Dibal-H / toluene / -78 °C

2.1: Et₃N; DMAP / CH₂Cl₂

3.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

4.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 760 Torr

5.1: B-bromocatecholborane / CH₂Cl₂

6.1: toluene / Heating

7.1: 80 percent / KH / tetrahydrofuran

8.1: n-BuLi / tetrahydrofuran / -78 °C

8.2: 78 percent / tetrahydrofuran / -78 °C

9.1: t-BuLi / tetrahydrofuran / -78 °C

9.2: 60 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

10.1: 76 percent / TBAF / tetrahydrofuran

11.1: TPAP; NMO / CH₂Cl₂

12.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

13.1: 65 percent / EDC; HOBt; i-Pr₂NEt / dimethylformamide

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; bromocatecholborane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0960-894X(02)00612-1