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

Base Information

Chemical Name:(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one
CAS No.:1333388-41-2
Molecular Formula:C₂₀H₂₅NO₄
Molecular Weight:343.423
Hs Code.:

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

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

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

There total 6 articles about (3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-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: 60.0%

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

: (8R,8aS)-8-(benzyloxy)-3-(4-methyl-5-oxotetrahydrofuran-2-yl)hexahydroindolizin-5(1H)-one

: 1333388-41-2
(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: With sodium tetrahydroborate; nickel dichloride; In methanol; at 0 - 20 ℃; for 1h;
DOI:10.1021/ol202140y

Reference yield:

: 1254985-48-2
(R)-1-allyl-3-benzyloxy-2,6-piperidinedione

: (8R,8aS)-8-(benzyloxy)-3-(4-methyl-5-oxotetrahydrofuran-2-yl)hexahydroindolizin-5(1H)-one

: 1333388-41-2
(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran; dichloromethane / 1 h / 0 °C

1.2: Saturated solution

1.3: 3 h / -78 °C

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

2.2: 3 h / Reflux

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C

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

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

6.1: sodium tetrahydroborate; nickel dichloride / methanol / 1 h / 0 - 20 °C

With dmap; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; rhodium(III) trichloride hydrate; triethylamine; nickel dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; dimethyl sulfoxide; 5.1: Vinylogous Mannich reaction;
DOI:10.1021/ol202140y

Reference yield:

: 1333388-38-7
(8R,8aS)-8-(benzyloxy)-3-hydroxyhexahydroindolizin-5(1H)-one

: (8R,8aS)-8-(benzyloxy)-3-(4-methyl-5-oxotetrahydrofuran-2-yl)hexahydroindolizin-5(1H)-one

: 1333388-41-2
(3S,8R,8aS)-8-(benzyloxy)-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]hexahydroindolizin-5(1H)-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: sodium tetrahydroborate; nickel dichloride / methanol / 1 h / 0 - 20 °C

With dmap; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; triethylamine; nickel dichloride; In methanol; dichloromethane; 2: Vinylogous Mannich reaction;
DOI:10.1021/ol202140y