(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

Base Information

Chemical Name:(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester
CAS No.:397883-97-5
Molecular Formula:C₂₁H₂₈N₂O₆
Molecular Weight:404.463
Hs Code.:

Synonyms:(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

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Chemical Property of (3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

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Technology Process of (3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

There total 5 articles about (3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-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: 75.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 397883-91-9
(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3-carboxylic acid tert-butyl ester

: 397883-97-5
(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

Guidance literature:: (3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3-carboxylic acid tert-butyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

benzyl chloroformate; In tetrahydrofuran; hexane; at -78 ℃; for 0.416667h; Further stages.;
DOI:10.1021/ol010221p

Reference yield:

: 366450-25-1
(4S,5R)-4-hydroxy-5-methanesulfonyloxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 397883-97-5
(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / NaN₃ / dimethylformamide / 22 h / 45 °C

2.1: H₂ / Pd/C / methanol / 44 h

2.2: 100 percent / methanol / 24 h / 65 °C

3.1: 95 percent / TsOH / acetone / 40 h / 20 °C

4.1: nBuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: 75 percent / tetrahydrofuran; hexane / 0.42 h / -78 °C

With n-butyllithium; sodium azide; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol010221p

Reference yield:

: 366450-24-0
(4S,5R)-4-hydroxy-5-hydroxymethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 397883-97-5
(3aR,7aS)-2,2-dimethyl-6-oxo-perhydrooxazolo[4,5-c]pyridine-3,5-dicarboxylic acid-5-benzyl ester-3-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / pyridine / 0.42 h / -5 - 0 °C

2.1: 90 percent / NaN₃ / dimethylformamide / 22 h / 45 °C

3.1: H₂ / Pd/C / methanol / 44 h

3.2: 100 percent / methanol / 24 h / 65 °C

4.1: 95 percent / TsOH / acetone / 40 h / 20 °C

5.1: nBuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: 75 percent / tetrahydrofuran; hexane / 0.42 h / -78 °C

With n-butyllithium; sodium azide; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol010221p