2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid

Base Information

• Chemical Name: 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid
• CAS No.: 1316164-03-0
• Molecular Formula: C₂₃H₂₂N₂O₆S
• Molecular Weight: 454.503

Synonyms:2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid

Chemical Property of 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid

Chemical Property:

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Technology Process of 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid

There total 2 articles about 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid 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: 48.0%

benzyl (-)-(2S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (59034-30-9) → 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid (1316164-03-0)

Guidance literature:

With sodium sulfide nonahydrate; In tetrahydrofuran; water; at 0 - 5 ℃; for 0.25h;

DOI:10.1002/ejoc.201100148

Reference yield:

C23H20Cl2N2O5S → 2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid (1316164-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tin(ll) chloride / tetrahydrofuran / 3 h / 20 °C

2: sodium sulfide nonahydrate / tetrahydrofuran; water / 0.25 h / 0 - 5 °C

With sodium sulfide nonahydrate; tin(ll) chloride; In tetrahydrofuran; water;

DOI:10.1002/ejoc.201100148

Reference yield: 45.0%

2-[(2S,5S,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid (1316164-03-0) → benzyl (2S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (1316164-09-6)

Guidance literature:

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

DOI:10.1002/ejoc.201100148

upstream raw materials:

benzyl (-)-(2S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Downstream raw materials:

benzyl (2S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

benzyl (2S,5S,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

benzyl (2S,5S,6R)-6-[(N-decanoyl-L-prolyl-L-threonyl-L-alanyl-L-asparaginyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylate

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