N-[1-[(Z)-4-((4R,5R)-5-Azido-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-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl)-but-3-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide
• CAS No.: 884335-05-1
• Molecular Formula: C₁₆H₂₂N₆O₆S₃
• Molecular Weight: 490.585

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about N-[1-[(Z)-4-((4R,5R)-5-Azido-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: 74.0%

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) → N-[1-[(Z)-4-((4R,5R)-5-Azido-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl)-but-3-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-05-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In dichloromethane; tert-butyl alcohol;

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-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl)-but-3-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-05-1)

Guidance literature:

Multi-step reaction with 8 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

8: 74 percent / (NH₄)2Ce(NO₃)6 / CH₂Cl₂; 2-methyl-propan-2-ol

With pyridine; dmap; sodium azide; ammonium cerium(IV) nitrate; 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; tert-butyl alcohol;

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-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl)-but-3-enylamino]-1-methylsulfanyl-meth-(Z)-ylidene]-4-methoxy-benzenesulfonamide (884335-05-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

2: Me₃P; H₂O / tetrahydrofuran

3: iPr₂NEt / acetonitrile

4: pyridine; DMAP / CH₂Cl₂

5: NaN₃ / dimethylformamide / -15 °C

6: 74 percent / (NH₄)2Ce(NO₃)6 / CH₂Cl₂; 2-methyl-propan-2-ol

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

DOI:10.1021/ja0608545

upstream raw materials:

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

(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

Downstream raw materials:

Carbamic acid (3R,4S,4aR,5S)-4-({amino-[(E)-4-methoxy-benzenesulfonylimino]-methyl}-amino)-4a,5-dihydroxy-1-[(E)-4-methoxy-benzenesulfonylimino]-octahydro-pyrrolo[1,2-c]pyrimidin-3-ylmethyl ester

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

C₂₄H₃₂N₈O₇S₃

C₂₄H₃₄N₆O₇S₃

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