(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

Base Information

Chemical Name:(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid
CAS No.:192061-14-6
Molecular Formula:C₂₆H₂₇N₃O₁₂
Molecular Weight:573.513
Hs Code.:

(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

Synonyms:(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

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Chemical Property of (1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

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Technology Process of (1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

There total 12 articles about (1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid 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: 83.0%

: 263138-94-9
(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

: 192061-14-6
(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 2h;
DOI:10.1016/S0040-4020(99)01046-7

Reference yield:

: 125229-14-3
methyl 3-methoxymethyloxy-4-methyl-5-nitrobenzene

: 192061-14-6
(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / NaOMe / methanol; dimethylformamide / 3.5 h

2: 96 percent / imidazole / dimethylformamide / 24 h

3: 93 percent / DDQ; H₂O / CH₂Cl₂ / 1.5 h

4: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 2.5 h

5: H₂ / Pd/C / methanol / 0.13 h

6: MgSO₄; 4A molecular sieves / CH₂Cl₂ / Heating

7: 110 mg / NaCNBH₃; TFA / CH₂Cl₂; H₂O / 0.07 h

8: 88 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 4 h

9: 61 percent / DIBAL / CH₂Cl₂; hexane / 5 h / -78 °C

10: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

11: 14 mg / pyridine / 2.5 h

12: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Addition / 2: Substitution / 3: Substitution / 4: Oxidation / 5: Catalytic hydrogenation / 6: Cyclization / 7: Reduction / 8: Acylation / 9: Reduction / 10: Substitution / 11: Carboxylation / 12: Oxidation;
DOI:10.1016/S0040-4020(99)01046-7

Reference yield:

: 192061-07-7
[2S-(2α,3α)]-methyl ester 2-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-formyl-1-aziridinecarboxylic acid

: 192061-14-6
(1aS-cis)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 1-methyl ester 5-formyl-1a,8,9a-tetrahydro-7-(methoxymethoxy)-9-oxo-1H-aziridino[2,3-c][1]benzazocine-1,3(2H)-dicarboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd/C / methanol / 0.13 h

2: MgSO₄; 4A molecular sieves / CH₂Cl₂ / Heating

3: 110 mg / NaCNBH₃; TFA / CH₂Cl₂; H₂O / 0.07 h

4: 88 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 4 h

5: 61 percent / DIBAL / CH₂Cl₂; hexane / 5 h / -78 °C

6: 85 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7: 14 mg / pyridine / 2.5 h

8: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1: Catalytic hydrogenation / 2: Cyclization / 3: Reduction / 4: Acylation / 5: Reduction / 6: Substitution / 7: Carboxylation / 8: Oxidation;
DOI:10.1016/S0040-4020(99)01046-7