(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

Base Information

Chemical Name:(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one
CAS No.:494836-35-0
Molecular Formula:C₃₅H₄₄N₄O₃Si
Molecular Weight:596.845
Hs Code.:

Synonyms:(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

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Chemical Property of (1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

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Technology Process of (1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

There total 10 articles about (1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-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: 60.0%

: 494836-47-4
(1R,3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

: 494836-35-0
(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: (1R,3S,6S,8S,8aS)-6-Benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; at -78 ℃;
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

: 494836-35-0
(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 10 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

With dmap; n-butyllithium; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
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

: 494836-35-0
(1R,3S,6S,8S,8aS)-6-Azido-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-ethyl-8-methoxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 9 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

With dmap; n-butyllithium; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0960-894X(02)00612-1