(3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Base Information

• Chemical Name: (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• CAS No.: 332047-23-1
• Molecular Formula: C₁₇H₂₉NO₇S
• Molecular Weight: 391.486
• Mol file: 332047-23-1.mol

Synonyms:(3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Chemical Property of (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

There total 1 articles about (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 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: 98.0%

(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (1443055-47-7) + methanesulfonyl chloride (124-63-0) → (3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (332047-23-1)

Guidance literature:

With dmap; triethylamine; at 0 ℃; for 1h;

DOI:10.1016/j.tetasy.2013.04.016

Reference yield: 91.0%

(3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (332047-23-1) → ethyl (3R,4R,5R)-4,5-acetylimino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate (1268086-96-9) + (5R)-ethyl 5-acetylamino-3-(pentan-3-yloxy)cyclohexa-1,3-dienecarboxylate (1443055-48-8)

Guidance literature:

With sodium hydride; In dichloromethane; dimethyl sulfoxide; mineral oil; at 20 ℃; for 8h; Reagent/catalyst; Solvent;

DOI:10.1016/j.tetasy.2013.04.016

Reference yield:

(3R,4S,5R)-ethyl 5-acetylamino-4-methanesulfonyloxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (332047-23-1) → oseltamivir phosphate (204255-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / dichloromethane; dimethyl sulfoxide; mineral oil / 8 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.37 h / -15 °C

3.1: caesium carbonate / dimethyl sulfoxide / 0.25 h / 80 °C

3.2: 0.33 h / 80 °C

4.1: phosphoric acid / ethyl acetate; ethanol / 2 h / 50 °C

With phosphoric acid; boron trifluoride diethyl etherate; sodium hydride; caesium carbonate; In ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; mineral oil;

DOI:10.1016/j.tetasy.2013.04.016

upstream raw materials:

(3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

methanesulfonyl chloride

Downstream raw materials:

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

(5R)-ethyl 5-acetylamino-3-(pentan-3-yloxy)cyclohexa-1,3-dienecarboxylate

(3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate

oseltamivir phosphate