(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Base Information

Chemical Name:(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one
CAS No.:1333388-40-1
Molecular Formula:C₂₀H₂₃NO₄
Molecular Weight:341.407
Hs Code.:

Synonyms:(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

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Chemical Property of (8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Chemical Property:

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Technology Process of (8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

There total 5 articles about (8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-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:

: 1333388-37-6
(8R,8aS)-8-(benzyloxy)-5-oxo-octahydroindolizin-3-yl acetate

: 131497-06-8
tert-butyl(dimethyl)[(3-methylfuran-2-yl)oxy]silane

: 1333388-40-1
(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

: 1333388-39-8
(3S,8R,8aS)-8-(benzyloxy)-3-[(S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 2h; diastereoselective reaction;
DOI:10.1021/ol202140y

Reference yield:

: 1316831-98-7
(5R,6S)-1-allyl-5-(benzyloxy)-6-(3-hydroxypropyl)piperidin-2-one

: 1333388-40-1
(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: rhodium(III) trichloride hydrate / propan-1-ol / 3 h / Reflux

1.2: 3 h / Reflux

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C

3.1: dmap; triethylamine / 20 °C / Cooling with ice

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -78 - 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; rhodium(III) trichloride hydrate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In propan-1-ol; dichloromethane; dimethyl sulfoxide; 4.1: Vinylogous Mannich reaction;
DOI:10.1021/ol202140y

Reference yield:

: 1316832-00-4
(5R,6S)-5-(benzyloxy)-6-(3-hydroxypropyl)piperidin-2-one

: 1333388-40-1
(8R,8aS)-8-(benzyloxy)-3-[4-methyl-5-oxo-2,5-dihydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C

2: dmap; triethylamine / 20 °C / Cooling with ice

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -78 - 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; 3: Vinylogous Mannich reaction;
DOI:10.1021/ol202140y