(1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester
• CAS No.: 217824-86-7
• Molecular Formula: C₁₆H₁₉NO₅S
• Molecular Weight: 337.397
• Mol file: 217824-86-7.mol

Synonyms:(1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Chemical Property of (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester

There total 1 articles about (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl 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: 74.0%

2-thiopyridyl chloroformate (73371-99-0) + (3S*,5R*)-cis-3,5-bis(methoxycarbonyl)cyclohexanecarboxylic acid (196303-52-3) → (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester (217824-86-7)

Guidance literature:

With TEA; In dichloromethane; at 0 ℃;

DOI:10.1055/s-1998-3143

Reference yield: 65.0%

(4-(benzyloxy)phenyl)magnesium bromide (120186-59-6) + (1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester (217824-86-7) → (1R,3S,5R)-5-(4-Benzyloxy-benzoyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester (217824-80-1)

Guidance literature:

In tetrahydrofuran; at -30 ℃;

DOI:10.1055/s-1998-3143

Reference yield:

(1S,3R,5S)-5-(Pyridin-2-ylsulfanylcarbonyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester (217824-86-7) → (1S,3R,5S)-3-Hydroxymethyl-5-[4-(4-methoxy-benzyloxy)-benzyl]-cyclohexanecarboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / tetrahydrofuran / -30 °C

2: H₂ / 10percentPd/C / acetic acid / 50 °C / 3000.2 Torr

3: TBAI, Na₂CO₃ / acetone / 55 °C

4: 80 percent / L-Selectride / tetrahydrofuran / -78 °C

With hydrogen; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium carbonate; 10% palladium on active carbon; In tetrahydrofuran; acetic acid; acetone;

DOI:10.1055/s-1998-3143

upstream raw materials:

2-thiopyridyl chloroformate

(3S*,5R*)-cis-3,5-bis(methoxycarbonyl)cyclohexanecarboxylic acid

Downstream raw materials:

(1R,3S,5R)-5-(4-Benzyloxy-benzoyl)-cyclohexane-1,3-dicarboxylic acid dimethyl ester

(1R,3S,5R)-5-[4-(4-Methoxy-benzyloxy)-benzyl]-cyclohexane-1,3-dicarboxylic acid dimethyl ester