(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

Base Information

Chemical Name:(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile
CAS No.:1325729-81-4
Molecular Formula:C₂₀H₂₁IN₂O₂
Molecular Weight:448.303
Hs Code.:

Synonyms:(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

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Chemical Property of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

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Technology Process of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

There total 5 articles about (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-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: 75.0%

: 1325729-79-0
(2S,3R,4R)-2-amino-3,4-dibenzyloxyhex-5-enenitrile

: 1325729-81-4
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

Guidance literature:: With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;
DOI:10.1002/ejoc.201100523

Reference yield:

: 1325729-79-0
(2S,3R,4R)-2-amino-3,4-dibenzyloxyhex-5-enenitrile

: 1325729-81-4
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

: 1325729-82-5
(5S,6R,7R,7aS)-6,7-dibenzyloxy-3-oxotetrahydropyrrolo[1,2-c]oxazole-5-carbonitrile

Guidance literature:: With iodine; sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 4h; Under air;
DOI:10.1002/ejoc.201100523

Reference yield:

: 1239357-29-9
5-deoxy-5-iodo-D-arabinofuranoside

: 1325729-81-4
(2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-iodomethylpyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: acetic acid; zinc / ethanol; water / 2 h / Under air; Reflux

2: aluminum oxide / acetonitrile / 336 h / 20 °C / Under air

3: trifluoroacetic acid / Under air

4: N-iodo-succinimide / dichloromethane / 5 h / 20 °C / Inert atmosphere

With aluminum oxide; N-iodo-succinimide; acetic acid; trifluoroacetic acid; zinc; In ethanol; dichloromethane; water; acetonitrile; 1: Vasella reaction / 2: Strecker reaction;
DOI:10.1002/ejoc.201100523