benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 85339-59-9
• Molecular Formula: C₃₂H₃₂N₂O₇S₂
• Molecular Weight: 620.747
• Mol file: 85339-59-9.mol

Synonyms:

Chemical Property of benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 3 articles about benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-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: 26.0%

monobenzyl 3-thienylmalonic acid chloride (50893-38-4) + benzyl (2S,5R,6R)-6-amino-(E)-7-methoxycarbonylmethylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (112711-40-7) → benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85339-59-9,112711-41-8,112711-44-1,112790-55-3) + benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(E)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (112790-55-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

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)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85339-59-9,112711-41-8,112711-44-1,112790-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 12 percent / toluene / 18 h / Heating

2: 41 percent / triethylamine / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

Reference yield:

3-thienylmalonic acid monobenzyl ester (21080-93-3) → benzyl (2S,5R,6R)-6--7-methoxycarbonyl-(Z)-methylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85339-59-9,112711-41-8,112711-44-1,112790-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

2: 41 percent / triethylamine / tetrahydrofuran; dimethylformamide / 2 h / 20 °C

With oxalyl dichloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

monobenzyl 3-thienylmalonic acid chloride

benzyl (2S,5R,6R)-6-amino-(E)-7-methoxycarbonylmethylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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

3-thienylmalonic acid monobenzyl ester

Downstream raw materials:

benzyl 6β-penicillanate