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

Base Information

• Chemical Name: (-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide
• CAS No.: 196503-53-4
• Molecular Formula: C₁₅H₁₅NO₅S
• Molecular Weight: 321.354

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

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

Chemical Property:

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

There total 3 articles about (-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide 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: 97.0%

(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) → (-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.03,7]nonane-9-exo-carboxamide (196503-53-4)

Guidance literature:

With Oxone; In methanol; water; for 2h; Ambient temperature;

DOI:10.1055/s-1997-942

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-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.03,7]nonane-9-exo-carboxamide (196503-53-4)

Guidance literature:

Multi-step reaction with 3 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

3: 93.8 percent / Oxon^R₈ / methanol; H₂O / 2 h / Ambient temperature

With Oxon^R₈; propylphosphonic anhydride; ammonia; triethylamine; In methanol; dichloromethane; water;

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

Reference yield:

(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-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.03,7]nonane-9-exo-carboxamide (196503-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91.2 percent / Et₃N, propylphosphonic anhydride, NH₃ / CH₂Cl₂ / 0.08 h / 0 °C

2: 93.8 percent / Oxon^R₈ / methanol; H₂O / 2 h / Ambient temperature

With Oxon^R₈; propylphosphonic anhydride; ammonia; triethylamine; In methanol; dichloromethane; water;

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 amide

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

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

Downstream raw materials:

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

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]

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