(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Base Information

Chemical Name:(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester
CAS No.:697289-96-6
Molecular Formula:C₂₂H₂₆N₂O₉
Molecular Weight:462.456
Hs Code.:

(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Chemical Property of (1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

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Technology Process of (1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

There total 5 articles about (1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-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:

: 697289-70-6
ethyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-methoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylate

: 697289-96-6
(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: With sodium periodate; In water; acetone; at 0 - 20 ℃;
DOI:10.1002/ejoc.200300700

Reference yield:

: 134984-63-7
(1S,3S,4R)-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester

: 697289-96-6
(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: K₃Fe(CN)6; K₂CO₃; K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

2: 31.3 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

3: 42 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

4: NaIO₄ / acetone; H₂O / 0 - 20 °C

With sodium periodate; potassium dioxotetrahydroxoosmate(VI); hydrogen; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; potassium hexacyanoferrate(III); palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1002/ejoc.200300700

Reference yield:

: (1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester

: 697289-96-6
(1R,3S,6S,7S,8aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 31.3 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

2: 42 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

3: NaIO₄ / acetone; H₂O / 0 - 20 °C

With sodium periodate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.200300700