tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Base Information

Chemical Name:tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate
CAS No.:1007125-07-6
Molecular Formula:C₂₅H₂₅NO₇
Molecular Weight:451.476
Hs Code.:

Synonyms:tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

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Chemical Property of tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

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Technology Process of tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

There total 5 articles about tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate 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: 86.0%

: 1007125-06-5
(-)-(1R,4S,5R,6S)-tert-butyl 5,6-dihydroxy-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

: 98-88-4
benzoyl chloride

: 1007125-07-6
tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: With dmap; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo500382v

Reference yield:

: 151792-53-9
tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

: 1007125-07-6
tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; tert-butyl alcohol / 2 h / 0 - 20 °C

2: dmap / dichloromethane / 1 h / 0 °C

With dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1021/jo500382v

Reference yield:

: 49805-30-3
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

: 1007125-07-6
tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap / tetrahydrofuran / 20 °C

2: Savinase / tetrahydrofuran; aq. phosphate buffer / 48 h / 20 - 30 °C / pH 8.0 / Enzymatic reaction

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; tert-butyl alcohol / 2 h / 0 - 20 °C

4: dmap / dichloromethane / 1 h / 0 °C

With dmap; Savinase; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1021/jo500382v