(2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide

Base Information

• Chemical Name: (2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide
• CAS No.: 1352791-72-0
• Molecular Formula: C₄₁H₄₇N₃O₆S
• Molecular Weight: 709.907

Synonyms:(2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide

Chemical Property of (2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide

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Technology Process of (2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide

There total 9 articles about (2R)-N₄-benzyloxy-2-[3-(benzyloxy)benzyl]-N₁-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide 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: 85.0%

tert-butyl (3R)-3-[3-(benzyloxy)benzyl]-4-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-ylamino]-4-oxobutanoate (1352791-78-6) + O-benzylhydoxylamine hydrochloride (2687-43-6) → (2R)-N4-benzyloxy-2-[3-(benzyloxy)benzyl]-N1-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide (1352791-72-0)

Guidance literature:

tert-butyl (3R)-3-[3-(benzyloxy)benzyl]-4-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-ylamino]-4-oxobutanoate; With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 3h;

O-benzylhydoxylamine hydrochloride; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

DOI:10.1002/ejoc.201100868

Reference yield:

C22H34N2O5S2 → (2R)-N4-benzyloxy-2-[3-(benzyloxy)benzyl]-N1-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide (1352791-72-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

2.1: methoxybenzene / dichloromethane / 0 °C

3.1: C₁₈H₃₄N₆P⁽¹⁺⁾*F₆P^(1-); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h

4.1: trifluoroacetic acid / dichloromethane; water / 3 h / 20 °C

4.2: 0.25 h / 0 °C

With C₁₈H₃₄N₆P⁽¹⁺⁾*F₆P^(1-); diisobutylaluminium hydride; methoxybenzene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201100868

Reference yield:

tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate (1352791-77-5) → (2R)-N4-benzyloxy-2-[3-(benzyloxy)benzyl]-N1-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-yl]succinamide (1352791-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h

2.1: C₁₈H₃₄N₆P⁽¹⁺⁾*F₆P^(1-); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h

3.1: trifluoroacetic acid / dichloromethane; water / 3 h / 20 °C

3.2: 0.25 h / 0 °C

With C₁₈H₃₄N₆P⁽¹⁺⁾*F₆P^(1-); dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201100868

upstream raw materials:

(3R)-2-[3-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid

tert-butyl 3-[3-(benzyloxy)phenyl]propanoate

tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate

tert-butyl (3R)-3-[3-(benzyloxy)benzyl]-4-[(1S,2R,3R,3aS,7aR)-2-hydroxy-3-{(S)-N-methylphenylsulfonimidoyl}octahydro-1H-inden-1-ylamino]-4-oxobutanoate

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