(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

Base Information

• Chemical Name: (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide
• CAS No.: 196503-52-3
• Molecular Formula: C₁₅H₁₅NO₃S
• Molecular Weight: 289.355
• Mol file: 196503-52-3.mol

Synonyms:(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

Chemical Property of (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide

There total 3 articles about (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide 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: 91.2%

(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.03,7]nonane-9-carboxylic acid (196503-51-2) → (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.03,7]nonane-9-carboxylic acid amide (196503-52-3)

Guidance literature:

With propylphosphonic anhydride; ammonia; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T

Reference yield:

(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid (70190-87-3) → (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.03,7]nonane-9-carboxylic acid amide (196503-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.4 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2: 91.2 percent / Et₃N, propylphosphonic anhydride, NH₃ / CH₂Cl₂ / 0.08 h / 0 °C

With propylphosphonic anhydride; ammonia; triethylamine; In dichloromethane;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T

Reference yield:

benzenesulfenyl chloride (931-59-9) → (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.03,7]nonane-9-carboxylic acid amide (196503-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.4 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2: 91.2 percent / Et₃N, propylphosphonic anhydride, NH₃ / CH₂Cl₂ / 0.08 h / 0 °C

With propylphosphonic anhydride; ammonia; triethylamine; In dichloromethane;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T

upstream raw materials:

(1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid

(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid

benzenesulfenyl chloride

Downstream raw materials:

(-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide

1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-cyano-3-formyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]

1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]

(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester