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

Base Information

Chemical Name:(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyl octanoate
CAS No.:1584664-41-4
Molecular Formula:C₃₀H₄₀N₂O₈
Molecular Weight:556.656
Hs Code.:

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

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

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

There total 8 articles about (3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyl octanoate 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: 78.0%

: 872369-26-1
(3S,4S)-4-nitrobenzyl 3-hydroxy-4-methyl octanoate

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 1584664-41-4
(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyl octanoate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.01.004

Reference yield:

: 872369-20-5
C₁₅H₃₂O₃Si

: 1584664-41-4
(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyl octanoate

Guidance literature:: Multi-step reaction with 3 steps

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

2: pyridine hydrogenfluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

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:

: 1584664-36-7
(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentan-1-one

: 1584664-41-4
(3S,4S)-4-nitrobenzyl 3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-4-methyl octanoate

Guidance literature:: Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

2: n-butyllithium / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

3: hydrogen; palladium 10% on activated carbon / ethanol / 12 h

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

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

6: pyridine hydrogenfluoride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

7: 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; diisobutylaluminium hydride; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile; 2: |Wittig Olefination;
DOI:10.1016/j.tetasy.2014.01.004