(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

Base Information

Chemical Name:(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one
CAS No.:1273550-78-9
Molecular Formula:C₁₉H₂₁NO₇
Molecular Weight:375.378
Hs Code.:

Synonyms:(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

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Chemical Property of (1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

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Technology Process of (1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

There total 4 articles about (1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one 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:

: C₁₅H₁₇NO₅

: 108-24-7
acetic anhydride

: (1S,2R,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

: 1273550-78-9
(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; optical yield given as %de; Inert atmosphere; Cooling with ice;
DOI:10.1016/j.tet.2010.12.048

Reference yield:

: C₁₈H₂₅NO₄Si

: (1S,2R,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

: 1273550-78-9
(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 20 °C / Inert atmosphere

2: Martins sulfurane / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere; Cooling with ice

3: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / Inert atmosphere; Cooling with ice

4: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

With dmap; osmium(VIII) oxide; Martins sulfurane; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1016/j.tet.2010.12.048

Reference yield:

: 1273550-77-8
(8S,8aR)-8-benzoyloxy-1-hydroxy-1,2,3,7,8,8a-hexahydro-6H-indolizin-5-one

: (1S,2R,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

: 1273550-78-9
(1R,2S,8S,8aS)-1,2-diacetoxy-8-benzoyloxy-1,2,3,7,8,8ahexahydro-6H-indolizin-5-one

Guidance literature:: Multi-step reaction with 3 steps

1: Martins sulfurane / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere; Cooling with ice

2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / Inert atmosphere; Cooling with ice

3: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

With dmap; osmium(VIII) oxide; Martins sulfurane; water; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1016/j.tet.2010.12.048