(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

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Chemical Name:(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether
CAS No.:142865-31-4
Molecular Formula:C₁₉H₂₄N₂O₅
Molecular Weight:360.41
Hs Code.:

Synonyms:(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

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Chemical Property of (2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

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Technology Process of (2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

There total 6 articles about (2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether 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: 26.0%

: 100-39-0
benzyl bromide

: 142800-11-1
(2S,5aS,10aS)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione

: 142865-31-4
(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

: 142800-15-5
(2S,5aS,10aS)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 23 ℃; for 1h;
DOI:10.1021/jo00045a050

Reference yield:

: 64187-47-9
1-benzyloxycarbonyl-4-keto-L-proline

: 142865-31-4
(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl chloride / benzene / 4 h / Heating

2: AgCN / toluene / Ambient temperature

3: NaBH₄, Al₂O₃ / methanol / 1 h / 23 °C

4: H₂ / 10percent Pd/C / methanol / 9 h / 2585.7 Torr

5: 24 percent / NaH, Bu₄NI / tetrahydrofuran / 1 h / 23 °C

With aluminum oxide; sodium tetrahydroborate; silver cyanide; oxalyl dichloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene; benzene;
DOI:10.1021/jo00045a050

Reference yield:

: 113490-85-0
4,4-dimethoxy-(S)-proline methyl ester

: 142865-31-4
(2S,5aR,10aR)-octahydro-2-hydroxy-7,7-dimethoxy-1H,5H-dipyrrolo<1,2-a:1',2'-d>pyrazine-5,10-dione, O-benzyl ether

Guidance literature:: Multi-step reaction with 4 steps

1: AgCN / toluene / Ambient temperature

2: NaBH₄, Al₂O₃ / methanol / 1 h / 23 °C

3: H₂ / 10percent Pd/C / methanol / 9 h / 2585.7 Torr

4: 24 percent / NaH, Bu₄NI / tetrahydrofuran / 1 h / 23 °C

With aluminum oxide; sodium tetrahydroborate; silver cyanide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00045a050