ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate
• CAS No.: 1350929-02-0
• Molecular Formula: C₁₂H₁₇N₃O₇S
• Molecular Weight: 347.349

Synonyms:ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

Chemical Property:

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Technology Process of ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate

There total 4 articles about ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 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: 95.0%

C11H15N3O5 (1350929-01-9) + methanesulfonyl chloride (124-63-0) → ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1350929-02-0)

Guidance literature:

With dmap; triethylamine; In ethyl acetate; at 0 ℃; for 1.25h;

DOI:10.1016/j.tetasy.2011.09.014

Reference yield:

C9H12O6S (1350928-94-7) → ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1350929-02-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 2.17 h / 20 °C

2: sodium azide; water / N,N-dimethyl-formamide / 24 h / 20 °C

3: dmap; triethylamine / ethyl acetate / 1.25 h / 0 °C

With dmap; sodium azide; water; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2011.09.014

Reference yield:

C11H14O7S (1350929-00-8) → ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate (1350929-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide; water / N,N-dimethyl-formamide / 24 h / 20 °C

2: dmap; triethylamine / ethyl acetate / 1.25 h / 0 °C

With dmap; sodium azide; water; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2011.09.014

upstream raw materials:

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

C₁₁H₁₅N₃O₅

methanesulfonyl chloride

C₉H₁₂O₆S

Downstream raw materials:

ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5R)-4-acetamido-5-acetoxy-3-(1-ethylpropoxy)-cyclohex-1-ene-1-carboxylate

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