(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Base Information

Chemical Name:(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester
CAS No.:111301-22-5
Molecular Formula:C₂₈H₃₃N₃O₉
Molecular Weight:555.585
Hs Code.:

(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Synonyms:(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

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Chemical Property of (2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

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Technology Process of (2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

There total 9 articles about (2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester 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:

: 20620-36-4
ethyl α-carbethoxyaminoacrylate

: 111301-22-5
(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

2: 1) LDA, 2) ZnCl₂ / 1) THF, -78 deg C, 2) THF, 0 deg C

3: H₂ / 10percent Pd/C / ethanol / 760 Torr

4: H₂ / 5percent Rh/C / ethyl acetate / 80 °C / 77572.2 Torr

5: K₂CO₃ / dimethylformamide / 80 °C

6: 1) H₂CrO₄, 2) K₂CO₃ / 1) acetone, room temp., 2) acetone, reflux

8: 79 percent / CSA, quinoline / benzene / Heating

9: 1) NOCl, 2) NaBH₃CN / 1) CH₃CN, CH₂Cl₂, -30 deg C; 2) MeOH, -30 to 0 deg C

With quinoline; camphor-10-sulfonic acid; hydrogen; chromic acid; sodium cyanoborohydride; potassium carbonate; nitrosylchloride; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; Rh on carbon; In ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)85425-8

Reference yield:

: 111301-17-8
5-Hydroxymethyl-2-methyl-4,5-dihydro-pyrrole-1,3-dicarboxylic acid 3-tert-butyl ester 1-ethyl ester

: 111301-22-5
(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1) LDA, 2) ZnCl₂ / 1) THF, -78 deg C, 2) THF, 0 deg C

2: H₂ / 10percent Pd/C / ethanol / 760 Torr

3: H₂ / 5percent Rh/C / ethyl acetate / 80 °C / 77572.2 Torr

4: K₂CO₃ / dimethylformamide / 80 °C

5: 1) H₂CrO₄, 2) K₂CO₃ / 1) acetone, room temp., 2) acetone, reflux

7: 79 percent / CSA, quinoline / benzene / Heating

8: 1) NOCl, 2) NaBH₃CN / 1) CH₃CN, CH₂Cl₂, -30 deg C; 2) MeOH, -30 to 0 deg C

With quinoline; camphor-10-sulfonic acid; hydrogen; chromic acid; sodium cyanoborohydride; potassium carbonate; nitrosylchloride; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; Rh on carbon; In ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)85425-8

Reference yield:

: 2-[2-Hydroxy-2-(5-hydroxy-2,4-dimethoxy-3-methyl-phenyl)-ethyl]-5-hydroxymethyl-4,5-dihydro-pyrrole-1,3-dicarboxylic acid 3-tert-butyl ester 1-ethyl ester

: 111301-22-5
(2R,3aR,6S,7aS)-6-(5-Benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-7-[(E)-hydroxyimino]-4-oxo-octahydro-pyrrolo[3,2-c]pyridine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 5percent Rh/C / ethyl acetate / 80 °C / 77572.2 Torr

2: K₂CO₃ / dimethylformamide / 80 °C

3: 1) H₂CrO₄, 2) K₂CO₃ / 1) acetone, room temp., 2) acetone, reflux

5: 79 percent / CSA, quinoline / benzene / Heating

6: 1) NOCl, 2) NaBH₃CN / 1) CH₃CN, CH₂Cl₂, -30 deg C; 2) MeOH, -30 to 0 deg C

With quinoline; camphor-10-sulfonic acid; hydrogen; chromic acid; sodium cyanoborohydride; potassium carbonate; nitrosylchloride; Rh on carbon; In ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)85425-8