20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

Base Information

Chemical Name:20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate
CAS No.:1357077-97-4
Molecular Formula:C₃₈H₅₅NO₇
Molecular Weight:640.833
Hs Code.:

Synonyms:20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

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Chemical Property of 20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

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Technology Process of 20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

There total 11 articles about 20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate 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: 93.0%

: 13574-13-5
Boc-Glu(OBzl)-OH

: 1357077-96-3
3α-hydroxy-5β-[9,12,12-(2)H3]pregnan-20-one

: 1357077-97-4
20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In benzene; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.steroids.2011.12.019

Reference yield:

: C₂₅H₃₅⁽²⁾H₃O₅

: 1357077-97-4
20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

2.2: 20 °C

3.1: 2 h

4.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / toluene / 4 h / Reflux; Inert atmosphere

5.1: hydrogenchloride; water / 0.25 h

6.1: pyridine; sodium tetrahydroborate; sodium hydroxide / methanol; water / Cooling with ice

7.1: dmap; dicyclohexyl-carbodiimide / benzene / 12 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; water; tri-n-butyl-tin hydride; dicyclohexyl-carbodiimide; sodium hydroxide; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; methanol; hexane; water; toluene; benzene; 4.1: Barton-McCombie reaction;
DOI:10.1016/j.steroids.2011.12.019

Reference yield:

: 1357077-93-0
3,20-bis(ethylenedioxy)-11β-hydroxy-5β-[9,12,12-(2)H3]pregnane

: 1357077-97-4
20-oxo-5β-[9,12,12-(2)H3]pregnan-3α-yl (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxo-pentanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

1.2: 20 °C

2.1: 2 h

3.1: tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile) / toluene / 4 h / Reflux; Inert atmosphere

4.1: hydrogenchloride; water / 0.25 h

5.1: pyridine; sodium tetrahydroborate; sodium hydroxide / methanol; water / Cooling with ice

6.1: dmap; dicyclohexyl-carbodiimide / benzene / 12 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; water; tri-n-butyl-tin hydride; dicyclohexyl-carbodiimide; sodium hydroxide; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; methanol; hexane; water; toluene; benzene; 3.1: Barton-McCombie reaction;
DOI:10.1016/j.steroids.2011.12.019