(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

Base Information

Chemical Name:(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine
CAS No.:675624-13-2
Molecular Formula:C₁₆H₂₇NO₄
Molecular Weight:297.395
Hs Code.:

Synonyms:(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

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Chemical Property of (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

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Technology Process of (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

There total 4 articles about (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine 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: 29.0%

: 823-76-7
Cyclohexyl methyl ketone

: (3R,4S,5R)-3,4-(isopropylidenedioxy)-5-[(5'R)-2'-methoxytetrahydrofuran-5'-yl]pyrrolidine

: 675624-13-2
(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

: (1S,2R,5S,8R,8aR)-5-[(1'S,2'R,8'R,8'aR)-1',2',8'-trihydroxy-1',2',3',7',8',8a'-hexahydro-6'-indolizinyl]-1,2,8-trihydroxy-indolizidine

Guidance literature:: With hydrogenchloride; In ethanol; for 32h; Heating;
DOI:10.1021/ol049947m

Reference yield:

: 182355-67-5
(5R)-5-[(1'S,2'R,3'R)-4'-azido-2',3'(isopropylidenedioxy)-1'-(methanesulfonyloxy)butyl]tetrahydrofuran-2-one

: 675624-13-2
(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / diisobutylaluminum hydride / CH₂Cl₂ / 3 h / -78 °C

2.1: 100 percent / aq. HCl / 20 °C

3.1: H₂ / Pd(OH)2/C / methanol / 3 h

3.2: 84 percent / Et₃N / methanol / 4 h / 60 °C

4.1: 29 percent / HCl / ethanol / 32 h / Heating

With hydrogenchloride; hydrogen; diisobutylaluminium hydride; palladium dihydroxide; In methanol; ethanol; dichloromethane; 4.1: Mannich reaction;
DOI:10.1021/ol049947m

Reference yield:

: Methanesulfonic acid (S)-((4R,5R)-5-azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-5-hydroxy-tetrahydro-furan-2-yl)-methyl ester

: 675624-13-2
(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(cyclohexyl)ethyl]-1,2,8-trihydroxy-indolizidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / aq. HCl / 20 °C

2.1: H₂ / Pd(OH)2/C / methanol / 3 h

2.2: 84 percent / Et₃N / methanol / 4 h / 60 °C

3.1: 29 percent / HCl / ethanol / 32 h / Heating

With hydrogenchloride; hydrogen; palladium dihydroxide; In methanol; ethanol; 3.1: Mannich reaction;
DOI:10.1021/ol049947m