3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Base Information

• Chemical Name: 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester
• CAS No.: 697290-23-6
• Molecular Formula: C₂₈H₃₈N₂O₉
• Molecular Weight: 546.618
• Mol file: 697290-23-6.mol

Synonyms:3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Chemical Property of 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

There total 1 articles about 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl 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: 100.0%

(1S,3S,4S)-2-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-5,6-dihydroxy-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester → 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester (697290-23-6)

Guidance literature:

(1S,3S,4S)-2-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-5,6-dihydroxy-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester; With sodium periodate; In water; acetone; at 0 - 20 ℃; for 0.5h;

In chloroform; at 20 ℃; for 14h;

DOI:10.1016/j.tetlet.2005.04.082

Reference yield: 21.0%

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) + 3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester (697290-23-6) → 3-(2-tert-butoxycarbonyl-ethyl)-7-(2-tert-butoxycarbonyl-vinyl)-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester + 1-(2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-3,5-bis-(2-tert-butoxycarbonyl-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (858359-69-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200300700

Reference yield:

3-(2-tert-butoxycarbonyl-ethyl)-7-formyl-1-hydroxy-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester (697290-23-6) → (3S,6S,7S,9S)-2-benzoyl-3,7-bis(2-carboxyethyl)-4-oxooctahydropyrrolo[1,2-a]pyrazine-6-carboxylic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 21 percent / tetrahydrofuran / 12 h / 20 °C

2: 83 percent / H₂ / Pd/C / ethanol / 24 h / 20 °C

3: DIPEA / CH₂Cl₂ / 3 h / 0 °C

4: TFA / CH₂Cl₂ / 3 h / 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1: Wittig olefination;

DOI:10.1002/ejoc.200300700

Downstream raw materials:

1-(2-benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-3,5-bis-(2-tert-butoxycarbonyl-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

2-benzoyl-3,7-bis-(2-tert-butoxycarbonyl-ethyl)-4-oxo-octahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid tert-butyl ester