(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

Base Information

Chemical Name:(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate
CAS No.:1584664-42-5
Molecular Formula:C₂₈H₄₄N₂O₈S
Molecular Weight:568.732
Hs Code.:

Synonyms:(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

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Chemical Property of (3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

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Technology Process of (3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

There total 8 articles about (3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate 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: 67.0%

: 2488-15-5
N-tert-butoxycarbonyl-L-methionine

: 1201179-80-7
(3S,4S)-4-nitrobenzyl 3-hydroxy-4-methyl decanoate

: 1584664-42-5
(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

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:

: (3S,4S)-3-[tert-butyl(dimethyl)silyloxy]-4-methyldecanoic acid

: 1584664-42-5
(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

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:

: 1464823-37-7
(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one

: 1584664-42-5
(3S,4S)-4-nitrobenzyl 3-((R)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoyloxy)-4-methyl decanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere; Cooling

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

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

3.2: Inert atmosphere; Cooling

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

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

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

7.1: pyridine hydrogenfluoride / tetrahydrofuran / Inert atmosphere; Cooling

8.1: 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; diisobutylaluminium hydride; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;
DOI:10.1016/j.tetasy.2014.01.004