O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate
• CAS No.: 114358-14-4
• Molecular Formula: C₂₀H₃₁NO₅Si
• Molecular Weight: 393.555

Synonyms:O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

Chemical Property of O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

Chemical Property:

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Technology Process of O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

There total 7 articles about O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate 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: 90.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + tert-butyldimethylsilyl chloride (18162-48-6) → O1-benzyl O2-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate (114358-14-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 24h;

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → O1-benzyl O2-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate (114358-14-4)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂

2: Et₃N / methanol

3: imidazole / dimethylformamide

With 1H-imidazole; thionyl chloride; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1246/cl.2007.550

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → O1-benzyl O2-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate (114358-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / acetonitrile / 15 h / 25 °C

2: imidazole / dimethylformamide / 15 h / 25 °C

With 1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo9708396

upstream raw materials:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

tert-butyldimethylsilyl chloride

(R)-4-hydroxy-L-proline ethyl ester

4R-4-hydroxyproline

Downstream raw materials:

(2S,4R)-1-benzyloxycarbonyl-4-<(tert-butyldimethylsilyl)oxy>-2-(hydroxymethyl)pyrrolidine

(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

(2R,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

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