benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 115234-84-9
• Molecular Formula: C₂₆H₂₇IN₂O₇S
• Molecular Weight: 638.48

Synonyms:benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 6 articles about benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-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:

benzyl (2S,3R,5R,6R)-3-hydroxymethyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115252-98-7) → benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115234-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / DMSO, oxalyl chloride, triethylamine / CH₂Cl₂ / -60 °C

2: ethyl acetate; diethyl ether / 1.) 0 deg C 5 h, 2.) room temp.12 h

3: trifluoroacetic anhydride, NaI / H₂O; acetonitrile / 1 h / Ambient temperature

4: 4-dimethylamino-pyridine / CH₂Cl₂ / 2.5 h

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; sodium iodide; In diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)90038-9

Reference yield:

benzyl (2S,3R,5R,6R)-3-formyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115234-74-7) → benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115234-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: ethyl acetate; diethyl ether / 1.) 0 deg C 5 h, 2.) room temp.12 h

2: trifluoroacetic anhydride, NaI / H₂O; acetonitrile / 1 h / Ambient temperature

3: 4-dimethylamino-pyridine / CH₂Cl₂ / 2.5 h

With dmap; trifluoroacetic anhydride; sodium iodide; In diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)90038-9

Reference yield:

benzyl (2S,3R,5R,6R)-3-methyl-3-oxiranyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115234-81-6) → benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (115234-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride, NaI / H₂O; acetonitrile / 1 h / Ambient temperature

2: 4-dimethylamino-pyridine / CH₂Cl₂ / 2.5 h

With dmap; trifluoroacetic anhydride; sodium iodide; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)90038-9

upstream raw materials:

acetic anhydride

(2S,3R,5R,6R)-3-(1-Hydroxy-2-iodo-ethyl)-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

benzyl (2S,3R,5R,6R)-3-hydroxymethyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

benzyl (2S,3R,5R,6R)-3-formyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Downstream raw materials:

benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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