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

Base Information

Chemical Name:(1R,2R,3R,5R,7S,8aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)-methyl]-5-methyloctahydroindolizin-7-ol
CAS No.:1400236-70-5
Molecular Formula:C₃₁H₃₇NO₄
Molecular Weight:487.639
Hs Code.:

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

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

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

There total 8 articles about (1R,2R,3R,5R,7S,8aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)-methyl]-5-methyloctahydroindolizin-7-ol 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: 75.0%

: C₃₀H₃₁NO₄

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

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 32 ℃; for 3h;
DOI:10.1021/jo3010777

Reference yield: 73.0%

: (2R,2'S,3aR,4R,5R,6R)-4,5-dibenzyloxy-6-(benzyloxymethyl)-2-(2-hydroxypropyl)-hexahydropyrrolo[1,2-b]isoxazole

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

Guidance literature:: (2R,2'S,3aR,4R,5R,6R)-4,5-dibenzyloxy-6-(benzyloxymethyl)-2-(2-hydroxypropyl)-hexahydropyrrolo[1,2-b]isoxazole; With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

With sodium hydrogencarbonate; sodium thiosulfate; In tetrahydrofuran; water; at 20 ℃; for 0.25h; Inert atmosphere;
DOI:10.1002/ejoc.201300103

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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