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

Base Information

• Chemical Name: (4R,5S)-4-((Z)-4-Azido-but-1-enyl)-3-(4-methoxy-benzyl)-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-5-ol
• CAS No.: 884335-04-0
• Molecular Formula: C₁₅H₂₀N₄O₅S
• Molecular Weight: 368.414
• Mol file: 884335-04-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(4R,5S)-4-((Z)-4-Azido-but-1-enyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-ol (884335-17-5) + p-methoxybenzyl chloride (824-94-2) → (4R,5S)-4-((Z)-4-Azido-but-1-enyl)-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-ol (884335-04-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In acetonitrile;

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) → (4R,5S)-4-((Z)-4-Azido-but-1-enyl)-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-ol (884335-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/CaCO₃/Pb / tetrahydrofuran

2: NaN₃; nBu₄NI / dimethylformamide

3: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

With sodium azide; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0608545

Reference yield:

Toluene-4-sulfonic acid (Z)-4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-4-yl)-but-3-enyl ester (884335-31-3) → (4R,5S)-4-((Z)-4-Azido-but-1-enyl)-3-(4-methoxy-benzyl)-2,2-dioxo-2λ6-[1,2,3]oxathiazinan-5-ol (884335-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃; nBu₄NI / dimethylformamide

2: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

With sodium azide; tetra-(n-butyl)ammonium iodide; potassium carbonate; In 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

p-methoxybenzyl chloride

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

C₂₄H₃₀N₈O₉S₄

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