(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

Base Information

Chemical Name:(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one
CAS No.:1357007-93-2
Molecular Formula:C₂₉H₃₁NO₅
Molecular Weight:473.569
Hs Code.:

Synonyms:(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

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Chemical Property of (1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

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Technology Process of (1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

There total 2 articles about (1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-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: 57.0%

: 1357007-89-6
(1R,2R,3R,7S,7aS)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-(dimethylphenylsilyl)pyrrolizidin-5-one

: 1357007-93-2
(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

Guidance literature:: With Cumene hydroperoxide; tetrabutyl ammonium fluoride; potassium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol203396s

Reference yield:

: 537030-19-6
(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

: 1357007-93-2
(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: samarium diiodide; 1,1,1,3',3',3'-hexafluoro-propanol; lithium bromide / tetrahydrofuran / 0.1 h / -78 - -30 °C / Inert atmosphere

1.2: 80 °C / Sonication; Inert atmosphere

2.1: Cumene hydroperoxide; tetrabutyl ammonium fluoride; potassium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

With samarium diiodide; 1,1,1,3',3',3'-hexafluoro-propanol; Cumene hydroperoxide; tetrabutyl ammonium fluoride; potassium hydride; lithium bromide; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Tamao-Fleming oxidation;
DOI:10.1021/ol203396s