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

Base Information

• Chemical Name: Toluene-4-sulfonic acid 4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl)-but-3-ynyl ester
• CAS No.: 884335-03-9
• Molecular Formula: C₁₄H₁₇NO₇S₂
• Molecular Weight: 375.423
• Mol file: 884335-03-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Toluene-4-sulfonic acid 4-((4R,5S)-5-hydroxy-2,2-dioxo-2λ⁶-[1,2,3]oxathiazinan-4-yl)-but-3-ynyl ester 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: 78.0%

(-)-(4R,7R)-6,6-dimethyltetrahydro-[1,3]dioxolo[4,5-d][1,2,3]oxathiazine 2,2-dioxide (884335-02-8) + 3-butyn-1-yl p-toluenesulfonate (23418-85-1) → 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)

Guidance literature:

3-butyn-1-yl p-toluenesulfonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 23 ℃;

(-)-(4R,7R)-6,6-dimethyltetrahydro-[1,3]dioxolo[4,5-d][1,2,3]oxathiazine 2,2-dioxide; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at 40 ℃; for 0.333333h; Further stages.;

DOI:10.1021/ja071501o

Reference yield:

(-)-(4R,7R)-6,6-dimethyltetrahydro-[1,3]dioxolo[4,5-d][1,2,3]oxathiazine 2,2-dioxide (884335-02-8) → 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)

Guidance literature:

With boron trifluoride diethyl etherate;

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,5S)-5-Hydroxy-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 (884335-19-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/CaCO₃/Pb / tetrahydrofuran

2: NaN₃; nBu₄NI / dimethylformamide

3: 85 percent / nBu₄NI; K₂CO₃ / acetonitrile

4: Me₃P; H₂O / tetrahydrofuran

5: iPr₂NEt / acetonitrile

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

DOI:10.1021/ja0608545

upstream raw materials:

(-)-(4R,7R)-6,6-dimethyltetrahydro-[1,3]dioxolo[4,5-d][1,2,3]oxathiazine 2,2-dioxide

3-butyn-1-yl p-toluenesulfonate

Downstream raw materials:

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

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

N-[1-{(Z)-4-[(4R,5S)-5-Hydroxy-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

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