(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate

Base Information

• Chemical Name: (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate
• CAS No.: 1201179-82-9
• Molecular Formula: C₃₂H₄₄N₂O₈
• Molecular Weight: 584.71

Synonyms:(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate

Chemical Property of (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate

Chemical Property:

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Technology Process of (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate

There total 8 articles about (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate 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: 86.0%

(3S,4S)-4-nitrobenzyl 3-hydroxy-4-methyl decanoate (1201179-80-7) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate (1201179-82-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2009.09.119

Reference yield:

(3S,4S)-3-[tert-butyl(dimethyl)silyloxy]-4-methyldecanoic acid → (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate (1201179-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere

2: pyridine hydrogenfluoride / tetrahydrofuran / Inert atmosphere; Cooling

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

With dmap; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2014.01.004

Reference yield:

(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (872369-17-0) → (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyldecanoate (1201179-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere; Cooling

2.1: hydrogen; palladium 10% on activated carbon / ethanol / 12 h / 20 °C

3.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 3 h / 20 °C / Inert atmosphere

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / tetrahydrofuran / Inert atmosphere; Cooling

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 8 h / 20 °C / Inert atmosphere

With dmap; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;

DOI:10.1016/j.tetasy.2014.01.004

upstream raw materials:

(3S,4S)-4-nitrobenzyl 3-hydroxy-4-methyl decanoate

N-tert-butoxycarbonyl-L-phenylalanine

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-one

Downstream raw materials:

C₂₇H₃₆N₂O₆

C₅₁H₇₀N₆O₁₂

(28S,29S)-arenamide A

C₂₇H₃₆N₂O₆*C₂HF₃O₂

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