Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl ester
• CAS No.: 199724-46-4
• Molecular Formula: C₁₄H₁₅NO₅S₃
• Molecular Weight: 373.475

Synonyms:Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl ester

Chemical Property of Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl ester

There total 7 articles about Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl 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: 85.0%

p-toluenesulfonylanhydride (4124-41-8) + (S)-2-Methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thieno[3,2-e][1,2]thiazin-4-ol → Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thieno[3,2-e][1,2]thiazin-4-yl ester (199724-46-4)

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/jo971550r

Reference yield:

1-(thiophen-3-yl)-ethanone (1468-83-3) → Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thieno[3,2-e][1,2]thiazin-4-yl ester (199724-46-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / H₂SO₄ / toluene / 2 h / Heating

2: 1.) BuLi, 2.) SO₂, 3.) Cl₂ / 1.) hexane, room temperature, 2 h, 2) -40 deg C to room temperature, overnight, 3.) H₂O, 15 min

3: tetrahydrofuran / -10 - 20 °C

4: HCl / acetone / 72 h / Ambient temperature

5: 74 percent / pyridinium bromide perbromide, HCl / tetrahydrofuran / 1.) 10 deg C, 30 min, 2.) 0 deg C, 1 h

6: 1.) (+)-Ipc₂BCl, 2.) diethanolamine, 3.) NaOH / 1.) THF, -25 deg C to room temperature, overnight, 2.) Me₂CO, 10 deg C, 6 h, 3.) Me₂CO, H₂O, room temperature, overnight

7: 85 percent / DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; (+)-β-chlorodiisopinocampheylborane; sulfuric acid; sulfur dioxide; pyridinium hydrobromide perbromide; chlorine; 2,2'-iminobis[ethanol]; In tetrahydrofuran; dichloromethane; acetone; toluene;

DOI:10.1021/jo971550r

Reference yield:

3-(2,5,5-Trimethyl-l,3-dioxane-2-yl)thiophene (138890-86-5) → Toluene-4-sulfonic acid (S)-2-methyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thieno[3,2-e][1,2]thiazin-4-yl ester (199724-46-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) BuLi, 2.) SO₂, 3.) Cl₂ / 1.) hexane, room temperature, 2 h, 2) -40 deg C to room temperature, overnight, 3.) H₂O, 15 min

2: tetrahydrofuran / -10 - 20 °C

3: HCl / acetone / 72 h / Ambient temperature

4: 74 percent / pyridinium bromide perbromide, HCl / tetrahydrofuran / 1.) 10 deg C, 30 min, 2.) 0 deg C, 1 h

5: 1.) (+)-Ipc₂BCl, 2.) diethanolamine, 3.) NaOH / 1.) THF, -25 deg C to room temperature, overnight, 2.) Me₂CO, 10 deg C, 6 h, 3.) Me₂CO, H₂O, room temperature, overnight

6: 85 percent / DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; (+)-β-chlorodiisopinocampheylborane; sulfur dioxide; pyridinium hydrobromide perbromide; chlorine; 2,2'-iminobis[ethanol]; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/jo971550r

upstream raw materials:

p-toluenesulfonylanhydride

1-(thiophen-3-yl)-ethanone

3-(2,5,5-Trimethyl-l,3-dioxane-2-yl)thiophene

3-acetyl-2-(methylaminosulfonyl)thiophene

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