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

Base Information

• Chemical Name: benzyl (2S,5R,6R)-6-amino-(E)-7-methoxycarbonylmethylene-3,3-dimethyl-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 112711-40-7
• Molecular Formula: C₁₈H₂₂N₂O₄S
• Molecular Weight: 362.45

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

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

Chemical Property:

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

There total 2 articles about benzyl (2S,5R,6R)-6-amino-(E)-7-methoxycarbonylmethylene-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: 19.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → 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)

Guidance literature:

In toluene;

Reference yield: 12.0%

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) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → 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)

Guidance literature:

In toluene; for 18h; Heating;

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;

upstream raw materials:

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

methyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

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

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

benzyl 6β-penicillanate

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