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

Base Information

Chemical Name:(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid
CAS No.:263138-97-2
Molecular Formula:C₂₄H₂₉N₃O₁₀
Molecular Weight:519.508
Hs Code.:

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

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

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Chemical Property of (1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

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Technology Process of (1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

There total 10 articles about (1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic 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: 85.0%

: 263138-93-8
(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

: 263138-97-2
(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(99)01046-7

Reference yield:

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

: 263138-97-2
(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 10 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

With 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;
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

: 263138-97-2
(1aS,9aS)-3-[(4,5-dimethoxy-2-nitrophenyl)methyl] 5-methanol-1a,2,3,8,9,9a-hexahydro-7-(methoxymethoxy)-9-hydroxy-1H-aziridino[2,3-c][1]benzazocine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

With dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; magnesium sulfate; 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;
DOI:10.1016/S0040-4020(99)01046-7