(2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• CAS No.: 131830-27-8
• Molecular Formula: C₁₆H₁₈N₂O₅S₂
• Molecular Weight: 382.461
• Mol file: 131830-27-8.mol

Synonyms:(2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Chemical Property of (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

There total 3 articles about (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 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: 58.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 6β-phenoxythiocarbamidopenicillanic acid 1β-sulfoxide (131830-24-5) → (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (131830-27-8)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

Reference yield:

6β-aminopenicillanic acid 1β-sulfoxide (33069-18-0) → (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (131830-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / 2 N aq. KOH / H₂O; tetrahydrofuran / 1 h

2: 58 percent / diethyl ether; tetrahydrofuran / 1 h / 0 °C

With potassium hydroxide; In tetrahydrofuran; diethyl ether; water;

Reference yield:

phenylcarbonochloridothioate (1005-56-7) → (2S,4S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenoxythiocarbonylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (131830-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / 2 N aq. KOH / H₂O; tetrahydrofuran / 1 h

2: 58 percent / diethyl ether; tetrahydrofuran / 1 h / 0 °C

With potassium hydroxide; In tetrahydrofuran; diethyl ether; water;

upstream raw materials:

diazomethane

6β-phenoxythiocarbamidopenicillanic acid 1β-sulfoxide

6β-aminopenicillanic acid 1β-sulfoxide

phenylcarbonochloridothioate

Downstream raw materials:

(R)-3-Methyl-2-((1R,5R)-7-oxo-3-phenoxy-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester

methyl 3-phenoxy-4,5-dithia-2,7-diazabicyclo<4.2.0>oct-2-ene-8-one-7-isopropenyl acetate