N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide

Base Information

• Chemical Name: N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide
• CAS No.: 884335-22-2
• Molecular Formula: C₂₄H₃₀N₆O₇S₃
• Molecular Weight: 610.736

Synonyms:N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide

Chemical Property of N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide

Chemical Property:

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Technology Process of N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide

There total 7 articles about N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide 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:

Trifluoro-methanesulfonic acid (4R,5S)-4-[(Z)-4-({[(Z)-4-methoxy-benzenesulfonylimino]-methylsulfanyl-methyl}-amino)-but-1-enyl]-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-yl ester → N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-22-2)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at -15 ℃;

DOI:10.1021/ja0608545

Reference yield:

Toluene-4-sulfonic acid 4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl)-but-3-ynyl ester (884335-03-9) → N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-22-2)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/CaCO₃/Pb / tetrahydrofuran

2: NaN₃; nBu₄NI / dimethylformamide

3: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

4: Me₃P; H₂O / tetrahydrofuran

5: iPr₂NEt / acetonitrile

6: pyridine; DMAP / CH₂Cl₂

7: NaN₃ / dimethylformamide / -15 °C

With pyridine; dmap; sodium azide; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; trimethylphosphane; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0608545

Reference yield:

(4R,5S)-4-((Z)-4-Azido-but-1-enyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-ol (884335-17-5) → N-[1-{(Z)-4-[(4R,5R)-5-Azido-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl]-but-3-enylamino}-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

2: Me₃P; H₂O / tetrahydrofuran

3: iPr₂NEt / acetonitrile

4: pyridine; DMAP / CH₂Cl₂

5: NaN₃ / dimethylformamide / -15 °C

With pyridine; dmap; sodium azide; water; tetra-(n-butyl)ammonium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; trimethylphosphane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0608545

upstream raw materials:

(4R,5S)-4-((Z)-4-Azido-but-1-enyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-5-ol

Toluene-4-sulfonic acid (Z)-4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl)-but-3-enyl ester

Toluene-4-sulfonic acid 4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl)-but-3-ynyl ester

(4R,5S)-4-((Z)-4-Azido-but-1-enyl)-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-5-ol

Downstream raw materials:

C₂₃H₃₀N₆O₇S₂

C₂₄H₃₄N₆O₇S₃

C₂₄H₃₂N₈O₇S₃

Carbamic acid (Z)-(4R,5R)-5-({amino-[(E)-4-methoxy-benzenesulfonylimino]-methyl}-amino)-2-[(Z)-4-methoxy-benzenesulfonylimino]-2,3,4,5,8,9-hexahydro-1H-[1,3]diazonin-4-ylmethyl ester

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