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

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile
• CAS No.: 1105054-55-4
• Molecular Formula: C₂₇H₂₈N₂O₃
• Molecular Weight: 428.531
• Mol file: 1105054-55-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-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: 85.0%

(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-5-carbonitrile (1105054-50-9) → (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-51-0) + (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-55-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 5h;

DOI:10.1016/j.tet.2008.10.096

Reference yield:

trimethylsilyl cyanide (7677-24-9) + (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one (158349-27-0) → (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-51-0) + (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-55-4)

Guidance literature:

(3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one; With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere;

trimethylsilyl cyanide; With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -25 - 20 ℃; Overall yield = 88 percent; Inert atmosphere;

DOI:10.3390/molecules26185459

Reference yield:

trimethylsilyl cyanide (7677-24-9) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole (397242-80-7) → (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-51-0) + (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile (1105054-55-4)

Guidance literature:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole; With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -40 ℃; for 0.166667h;

trimethylsilyl cyanide; In tetrahydrofuran; at -40 - 20 ℃;

DOI:10.1016/j.tet.2014.01.039

upstream raw materials:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-5-carbonitrile

trimethylsilyl cyanide

(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole

(3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one