(3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester
• CAS No.: 107302-13-6
• Molecular Formula: C₁₉H₂₅NO₈S
• Molecular Weight: 427.475

Synonyms:(3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester

Chemical Property of (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl ester

There total 11 articles about (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ⁶-[1,2]thiazine-2-carboxylic acid benzyl 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: 92.0%

β-epoxysultam (107302-12-5) + acetyl chloride (75-36-5) → (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ6-[1,2]thiazine-2-carboxylic acid benzyl ester (107302-13-6)

Guidance literature:

With potassium hydride; In tetrahydrofuran;

Reference yield:

3-(2,2-Dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,6-dihydro-1H-1λ6-[1,2]thiazine-2-carboxylic acid benzyl ester (107302-11-4) → (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ6-[1,2]thiazine-2-carboxylic acid benzyl ester (107302-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / CF₃CO₃H, K₂HPO₄ / CH₂Cl₂

2: 92 percent / KH / tetrahydrofuran

With dipotassium hydrogenphosphate; trifluoroacetyl peroxide; potassium hydride; In tetrahydrofuran; dichloromethane;

Reference yield:

sultam (107302-08-9) → (3R,4S)-4-Acetoxy-3-(2,2-dimethoxy-ethyl)-5-methyl-1,1-dioxo-3,4-dihydro-1H-1λ6-[1,2]thiazine-2-carboxylic acid benzyl ester (107302-13-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) AcOH, H₂O; 2.) PCC, alumina

2: methanolic HCl / methanol

3: 65 percent / CF₃CO₃H, K₂HPO₄ / CH₂Cl₂

4: 92 percent / KH / tetrahydrofuran

With hydrogenchloride; aluminum oxide; dipotassium hydrogenphosphate; trifluoroacetyl peroxide; water; potassium hydride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

β-epoxysultam

acetyl chloride

methyl 5-methyl-2,4-hexadienoate

(E)-methyl 5-methylhexa-3,5-dienoate

Downstream raw materials:

Acetic acid (1S,2S)-1-acetyl-2-benzyloxycarbonylamino-4,4-dimethoxy-butyl ester

Acetic acid (1S,2S)-1-acetyl-2-benzyloxycarbonylamino-4-oxo-butyl ester

Acetic acid (3R,4R)-4-benzyloxycarbonylamino-2,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester

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