1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-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-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]
CAS No.:196503-55-6
Molecular Formula:C₂₀H₂₀N₂O₅
Molecular Weight:368.389
Hs Code.:

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

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

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Technology Process of 1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-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-carbamoyl-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: 89.5%

: 41995-26-0
benzyl isocyanoacetate

: 196503-54-5
(1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 196503-55-6
1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T

Reference yield: 73.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: benzyl isocyanoacetate

: 196503-53-4
(-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide

: 196503-55-6
1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]

Guidance literature:: benzyl isocyanoacetate; (-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide; With potassium tert-butyl alcoholate; In tetrahydrofuran; at 20 ℃; for 1h;

diazomethane; In tetrahydrofuran; Further stages.;
DOI:10.1002/chem.200700222

Reference yield:

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

: 196503-55-6
1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate]

Guidance literature:: Multi-step reaction with 6 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

4: 1.) Ph₂Se₂, Na, 2.) <18>crown-6 / 24 h / Ambient temperature; 1.) THF, parrafin oil; 2.) THF

5: Ph₃P / CCl₄ / 18 h / Ambient temperature

6: 89.5 percent / t-BuOK / tetrahydrofuran / 1 h / Ambient temperature

With 18-crown-6 ether; Oxon^R₈; diphenyl diselenide; propylphosphonic anhydride; potassium tert-butylate; ammonia; sodium; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water;
DOI:10.1002/(SICI)1522-2675(19981111)81:11<1978::AID-HLCA1978>3.0.CO;2-T