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]

Base Information

• Chemical Name: 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]
• CAS No.: 952117-59-8
• Molecular Formula: C₂₁H₁₈N₂O₅
• Molecular Weight: 378.384
• Mol file: 952117-59-8.mol

Synonyms: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]

Chemical Property of 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]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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]

There total 7 articles about 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] 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: 60.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate] (196503-55-6) → 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] (952117-59-8)

Guidance literature:

With trichlorophosphate; at 80 ℃; for 2h;

DOI:10.1002/chem.200700222

Reference yield:

(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid (70190-87-3) → 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] (952117-59-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / Et₃N / CH₂Cl₂ / -78 deg C, 30 min then RT

2: 1) 1-propanephosphonic acid anhydride, Et₃N, 2) NH₃ / 1) CH₂Cl₂, 0 deg C, 2) CH₂Cl₂, 5 min, 0 deg C

3: 97 percent / oxone / H₂O; methanol / 2 h / Ambient temperature

4: 1) Ph₂Se₂, Na, 2) 18-crown-6 / 1) THF, 24 h, reflux, 2) THF, 24 h, RT

5: 71 percent / PPh₃, CCl₄ / 18 h / Ambient temperature

6: 1) t-BuOK / 1) THF, 2) THF, 3) THF, 1 h, RT

7: 1) POCl₃, 3) NaOAc, H₂O / 1) 15 deg C, 15 min, 2) DMF, 90 deg C, 45 min 3) 90 deg C, 15 min

With tetrachloromethane; Oxone; 18-crown-6 ether; diphenyl diselenide; potassium tert-butylate; ammonia; water; sodium acetate; sodium; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; triphenylphosphine; trichlorophosphate; In methanol; dichloromethane; water;

DOI:10.1055/s-1997-942

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) → 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] (952117-59-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) 1-propanephosphonic acid anhydride, Et₃N, 2) NH₃ / 1) CH₂Cl₂, 0 deg C, 2) CH₂Cl₂, 5 min, 0 deg C

2: 97 percent / oxone / H₂O; methanol / 2 h / Ambient temperature

3: 1) Ph₂Se₂, Na, 2) 18-crown-6 / 1) THF, 24 h, reflux, 2) THF, 24 h, RT

4: 71 percent / PPh₃, CCl₄ / 18 h / Ambient temperature

5: 1) t-BuOK / 1) THF, 2) THF, 3) THF, 1 h, RT

6: 1) POCl₃, 3) NaOAc, H₂O / 1) 15 deg C, 15 min, 2) DMF, 90 deg C, 45 min 3) 90 deg C, 15 min

With tetrachloromethane; Oxone; 18-crown-6 ether; diphenyl diselenide; potassium tert-butylate; ammonia; water; sodium acetate; sodium; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; triphenylphosphine; trichlorophosphate; In methanol; water;

DOI:10.1055/s-1997-942

upstream raw materials:

N,N-dimethyl-formamide

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

(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