trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Base Information

• Chemical Name: trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid
• CAS No.: 166666-96-2
• Molecular Formula: C₁₂H₁₁N₃O₆S
• Molecular Weight: 325.302
• Mol file: 166666-96-2.mol

Synonyms:trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Chemical Property of trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid

There total 4 articles about trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic 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:

1-(phenylsulfonyl)bicyclo[1.1.0]butane (80989-84-0) → trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (166666-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) hexane, THF, -78 deg C

2: 86 percent / N,N,N',N'-tetramethylguanidinium azide / dimethylformamide / 2 h / 80 - 90 °C

With n-butyllithium; N,N,N',N'-tetramethylguanidinium azide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80361-5

Reference yield:

3-Benzenesulfonyl-bicyclo[1.1.0]butane-1-carboxylic acid (124291-40-3) → trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (166666-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃, tetramethylguanidine / dimethylformamide / 6 h / 90 °C

2: 1.) BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT

With n-butyllithium; sodium azide; 1,1,3,3-tetramethylguanidine; In N,N-dimethyl-formamide;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + cis-1-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid (117488-20-7) → trans 1-azido-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid (166666-96-2)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT;

upstream raw materials:

carbon dioxide

cis-1-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid

3-Benzenesulfonyl-bicyclo[1.1.0]butane-1-carboxylic acid

1-(phenylsulfonyl)bicyclo[1.1.0]butane

Downstream raw materials:

Cis-ACBD

1-aminocyclobutane-cis-1,3-dicarboxylic acid

trans-1-amino-3-(phenylsulfonyl)cyclobutane-1,3-dicarboxylic acid