(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester
CAS No.:858367-21-2
Molecular Formula:C₂₁H₃₀N₂O₅
Molecular Weight:390.48
Hs Code.:

Synonyms:(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

There total 7 articles about (2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester 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:

: 858367-02-9
{[1-Cyclopropyl-meth-(E)-ylidene]-amino}-acetic acid methyl ester

: 858366-96-8
{[(E,3S,4S)-4-methyl-1-nitrohex-1-en-3-yloxy]methyl}benzene

: 858367-21-2
(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: With silver(I) acetate; triethylamine; In acetonitrile; at 20 ℃; for 5h;
DOI:10.1002/anie.200462497

Reference yield:

: 858366-85-5
(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol

: 858367-21-2
(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -70 - -60 °C

2: triethylamine / 16 h / 20 °C

3: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

4: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

With oxalyl dichloride; silver(I) acetate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; 2: Henry reaction;
DOI:10.1002/anie.200462497

Reference yield:

: 858366-75-3
methyl (2S,3S)-2-(benzyloxy)-3-methylpentanoate

: 858367-21-2
(2S,3R,4S,5S)-3-((1S,2S)-1-Benzyloxy-2-methyl-butyl)-5-cyclopropyl-4-nitro-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: lithium aluminum hydride / diethyl ether / 3 h / 20 °C

2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -70 - -60 °C

3: triethylamine / 16 h / 20 °C

4: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

5: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; silver(I) acetate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; acetonitrile; 3: Henry reaction;
DOI:10.1002/anie.200462497