17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate

Base Information

• Chemical Name: 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate
• CAS No.: 1408057-22-6
• Molecular Formula: C₄₀H₅₅F₅N₂O₇
• Molecular Weight: 770.878

Synonyms:17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate

Chemical Property of 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate

Chemical Property:

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Technology Process of 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate

There total 5 articles about 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate 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: 89.0%

Boc-Glu(OtBu)-OH (13726-84-6) + N-(3α-hydroxy-5β-androstan-17α-yl)-pentafluorobenzamide (1408057-21-5) → 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O5-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate (1408057-22-6)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; Inert atmosphere;

DOI:10.1016/j.steroids.2012.07.004

Reference yield:

3α-hydroxy-5β-androstan-17-one oxime (5615-34-9) → 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O5-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate (1408057-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 0.75 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

2.2: 0.83 h / 20 °C / Inert atmosphere

3.1: dmap; diisopropyl-carbodiimide / dichloromethane / Inert atmosphere

With dmap; sodium tetrahydroborate; nickel(II) chloride hexahydrate; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1016/j.steroids.2012.07.004

Reference yield:

C19H33NO → 17α-(pentafluorobenzoyl)amino-5β-androstan-3α-yl O5-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate (1408057-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

1.2: 0.83 h / 20 °C / Inert atmosphere

2.1: dmap; diisopropyl-carbodiimide / dichloromethane / Inert atmosphere

With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.steroids.2012.07.004

upstream raw materials:

Boc-Glu(OtBu)-OH

N-(3α-hydroxy-5β-androstan-17α-yl)-pentafluorobenzamide

3α-hydroxy-5β-androstan-17-one oxime

17α-azido-5β-androstan-3α-ol

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