(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

Base Information

Chemical Name:(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine
CAS No.:397883-99-7
Molecular Formula:C₂₀H₃₀N₂O₅S
Molecular Weight:410.535
Hs Code.:

Synonyms:(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

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Chemical Property of (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

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Technology Process of (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

There total 7 articles about (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine 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: 76.0%

: 397883-98-6
(4R,5S)-5-(3-benzenesulfonyl-2-oxopropyl)-4-(benzyloxycarbonylaminomethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 397883-99-7
(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

Guidance literature:: With hydrogen; palladium dihydroxide; In methanol; for 50h; under 760.051 Torr;
DOI:10.1021/ol010221p

Reference yield:

: 317819-12-8
(4S,5R)-5-tert-butoxycarbonylamino-4-hydroxy-2-oxo-piperidine

: 397883-99-7
(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / TsOH / acetone / 40 h / 20 °C

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

2.2: 75 percent / tetrahydrofuran; hexane / 0.42 h / -78 °C

3.1: 41 percent / tetrahydrofuran / 0.75 h / -76 °C

4.1: 76 percent / H₂ / Pd(OH)2 / methanol / 50 h / 760.05 Torr

With n-butyllithium; hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; 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

: 397883-99-7
(3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 7 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

6.1: 41 percent / tetrahydrofuran / 0.75 h / -76 °C

7.1: 76 percent / H₂ / Pd(OH)2 / methanol / 50 h / 760.05 Torr

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