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

Base Information

• Chemical Name: benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 65102-83-2
• Molecular Formula: C₂₃H₂₀N₂O₅S
• Molecular Weight: 436.488

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

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

Chemical Property:

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

There total 7 articles about benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-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: 70.0%

2-[(2S,5R,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid (65102-82-1) → benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (65102-83-2)

Guidance literature:

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

DOI:10.1002/ejoc.201100148

Reference yield:

phthalic anhydride (85-44-9) → benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (65102-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1.75 h

2: DCC / tetrahydrofuran / 18 h / Ambient temperature

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jo00401a012

Reference yield:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (3956-31-8,49626-54-2,64519-71-7) → benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (65102-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1.75 h

2: DCC / tetrahydrofuran / 18 h / Ambient temperature

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jo00401a012

upstream raw materials:

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

phthalic anhydride

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

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

Downstream raw materials:

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

benzyl (2S,5R,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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