(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile
CAS No.:1049770-50-4
Molecular Formula:C₂₇H₂₈N₂O₄
Molecular Weight:444.53
Hs Code.:

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

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Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

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Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

There total 7 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile 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: 100.0%

: 7677-24-9
trimethylsilyl cyanide

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

: 1049770-50-4
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

Guidance literature:: In methanol; at 20 ℃; for 10h; Inert atmosphere;
DOI:10.1002/ejoc.200800098

Reference yield: 88.0%

: 7677-24-9
trimethylsilyl cyanide

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

: 1049770-58-2
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

: 1049770-50-4
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

Guidance literature:: In methanol; at 50 ℃; for 8h;
DOI:10.1016/j.tet.2008.10.096

Reference yield:

: 620946-66-9
(E/Z)-2,3,5-tri-O-benzyl-D-arabinose-oxime

: 1049770-50-4
(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-1-hydroxypyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane / 1.5 h / 20 °C

2: 1H-imidazole; triphenylphosphine; iodine / toluene / 2.5 h / Inert atmosphere; Reflux

3: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

4: methanol / 4 h / 50 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/j.bioorg.2022.105650