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

Base Information

Chemical Name:(1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-hydroxy-hexahydro-indolizin-5-one
CAS No.:494836-43-0
Molecular Formula:C₃₄H₄₆N₄O₃Si
Molecular Weight:586.85
Hs Code.:

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

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

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

There total 9 articles about (1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-hydroxy-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:

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

: 494836-43-0
(1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 9 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: LiHMDS / tetrahydrofuran / -78 °C

6.2: 74 percent / tetrahydrofuran / -78 °C

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

7.2: 72 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

8.1: B-bromocatecholborane / CH₂Cl₂

9.1: toluene / Heating

With dmap; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; 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

: 494836-43-0
(1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 8 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: LiHMDS / tetrahydrofuran / -78 °C

5.2: 74 percent / tetrahydrofuran / -78 °C

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

6.2: 72 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

7.1: B-bromocatecholborane / CH₂Cl₂

8.1: toluene / Heating

With dmap; boron trifluoride diethyl etherate; bromocatecholborane; hydrogen; tert.-butyl lithium; 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:

: 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 494836-43-0
(1R,3S,6R,8S,8aS)-6-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-cyclohex-1-enylmethyl-1-ethyl-8-hydroxy-hexahydro-indolizin-5-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Et₃N; DMAP / CH₂Cl₂

2.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 760 Torr

4.1: LiHMDS / tetrahydrofuran / -78 °C

4.2: 74 percent / tetrahydrofuran / -78 °C

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

5.2: 72 percent / Trisyl-N₃ / tetrahydrofuran / -78 °C

6.1: B-bromocatecholborane / CH₂Cl₂

7.1: toluene / Heating

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