(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

Base Information

Chemical Name:(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester
CAS No.:459832-87-2
Molecular Formula:C₂₅H₂₇NO₄
Molecular Weight:405.494
Hs Code.:

Synonyms:(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

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Chemical Property of (3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

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Technology Process of (3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

There total 8 articles about (3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl 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: 91.0%

: 459833-02-4
4-[benzyl-(4-oxo-pent-2-enoyl)-amino]-5-phenyl-pent-2-enoic acid ethyl ester

: 459832-87-2
(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

Guidance literature:: In toluene; for 16h; Heating;
DOI:10.1016/j.tet.2003.04.007

Reference yield:

: 124818-94-6,116246-06-1
ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

: 459832-87-2
(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

2: 2.7 g / Cs₂CO₃ / CH₂Cl₂ / 12 h / 0 - 20 °C

3: 82 percent / EDCI; HOAT / dimethylformamide / 14 h / 0 - 20 °C

4: 91 percent / toluene / 16 h / Heating

With 1-hydroxy-7-aza-benzotriazole; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2003.04.007

Reference yield:

: 244033-83-8
(4S)-4-N-benzylamino-5-phenyl-2-trans-pentenoic acid, ethyl ester

: 459832-87-2
(3S,3aR,4S,7aR)-2,3-dibenzyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / EDCI; HOAT / dimethylformamide / 14 h / 0 - 20 °C

2: 91 percent / toluene / 16 h / Heating

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2003.04.007