1-Pyrrolidinecarboxylic acid, 2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-, 1,1-dimethylethyl ester, (2S,3R,5S)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-, 1,1-dimethylethyl ester, (2S,3R,5S)-
CAS No.:494836-33-8
Molecular Formula:C39H54N4O5Si
Molecular Weight:686.967
Hs Code.:

1-Pyrrolidinecarboxylic acid,
2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan
yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-,
1,1-dimethylethyl ester, (2S,3R,5S)-

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-, 1,1-dimethylethyl ester, (2S,3R,5S)-

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Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-, 1,1-dimethylethyl ester, (2S,3R,5S)-

There total 7 articles about 1-Pyrrolidinecarboxylic acid, 2-[(2S,4R)-4-azido-4-(1-cyclohexen-1-ylmethyl)tetrahydro-5-oxo-2-furan yl]-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-ethyl-, 1,1-dimethylethyl ester, (2S,3R,5S)- 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: 72.0%

: 494836-32-7
(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((2S,4R)-4-cyclohex-1-enylmethyl-5-oxo-tetrahydro-furan-2-yl)-3-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 494836-33-8
(2S,3R,5S)-2-((2S,4R)-4-Azido-4-cyclohex-1-enylmethyl-5-oxo-tetrahydro-furan-2-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((2S,4R)-4-cyclohex-1-enylmethyl-5-oxo-tetrahydro-furan-2-yl)-3-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester; 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

: 494836-33-8
(2S,3R,5S)-2-((2S,4R)-4-Azido-4-cyclohex-1-enylmethyl-5-oxo-tetrahydro-furan-2-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 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

With dmap; boron trifluoride diethyl etherate; 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

: 494836-33-8
(2S,3R,5S)-2-((2S,4R)-4-Azido-4-cyclohex-1-enylmethyl-5-oxo-tetrahydro-furan-2-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With dmap; boron trifluoride diethyl etherate; 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