(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

Base Information

Chemical Name:(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine
CAS No.:1400236-73-8
Molecular Formula:C₃₅H₃₉N₃O₄S
Molecular Weight:597.778
Hs Code.:

Synonyms:(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

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Chemical Property of (1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

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Technology Process of (1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

There total 3 articles about (1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine 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%

: 1400236-70-5
(1R,2R,3R,5R,7S,8aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)-methyl]-5-methyloctahydroindolizin-7-ol

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 1400236-73-8
(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

Guidance literature:: In tetrahydrofuran; for 6h; Reflux;
DOI:10.1021/jo3010777

Reference yield:

: 397242-80-7
(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole

: 1400236-73-8
(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

Guidance literature:: Multi-step reaction with 3 steps

1.1: ytterbium(III) triflate / dichloromethane / 0.17 h / -40 °C / Inert atmosphere

1.2: 3 h / -40 - 0 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 32 °C

3.1: tetrahydrofuran / 6 h / Reflux

With palladium 10% on activated carbon; hydrogen; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: |Diels-Alder Cycloaddition / 1.2: |Diels-Alder Cycloaddition;
DOI:10.1021/jo3010777

Reference yield:

: C₃₀H₃₁NO₄

: 1400236-73-8
(1R,2R,3R,5R,7S,8aR)-7-[(imidazolylthiocarbonyl)oxy]-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-5-methyloctahydroindolizine

Guidance literature:: Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 32 °C

2: tetrahydrofuran / 6 h / Reflux

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jo3010777