trans-4-(tert-Butyldiphenylsilyloxy)-L-proline

Base Information

• Chemical Name: trans-4-(tert-Butyldiphenylsilyloxy)-L-proline
• CAS No.: 259212-61-8
• Molecular Formula: C21H27NO3Si
• Molecular Weight: 369.536
• DSSTox Substance ID: DTXSID80468482
• Nikkaji Number: J1.224.350B
• Wikidata: Q82295690
• Mol file: 259212-61-8.mol

Synonyms:trans-4-(tert-Butyldiphenylsilyloxy)-L-proline;259212-61-8;(2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid;(2S,4R)-4-[tert-butyl(diphenyl)silyl]oxypyrrolidine-2-carboxylic acid;L-Proline, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (4R)-;(2S,4R)-4-[(TERT-BUTYLDIPHENYLSILYL)OXY]PYRROLIDINE-2-CARBOXYLIC ACID;C21H27NO3Si;SCHEMBL15674401;DTXSID80468482;(2S,4R)-4-(tert-Butyldiphenylsilyloxy)pyrrolidine-2-carboxylic Acid;MFCD12407126;AKOS015837847;AS-70995;B3440;CS-0046868;A877435;J-016184;(2S, 4R)-4-[tert-butyl(diphenyl)silyl]oxypyrrolidine-2-carboxylic acid

Chemical Property of trans-4-(tert-Butyldiphenylsilyloxy)-L-proline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 214-215 °C(Solv: methanol (67-56-1); hexane (110-54-3); ethyl ether (60-29-7))
• Boiling Point: 468.8±45.0 °C(Predicted)
• PKA: 2.04±0.40(Predicted)
• PSA: 58.56000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 2.70690
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 369.17602026
• Heavy Atom Count: 26
• Complexity: 460

Purity/Quality:

97% ^*data from raw suppliers

trans-4-(tert-Butyldiphenylsilyloxy)-L-proline >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC3CC(NC3)C(=O)O
• Isomeric SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)O[C@@H]3C[C@H](NC3)C(=O)O

Technology Process of trans-4-(tert-Butyldiphenylsilyloxy)-L-proline

There total 7 articles about trans-4-(tert-Butyldiphenylsilyloxy)-L-proline 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%

(2S,4R)-4-(tert-butyldiphenylsiloxy)pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (866327-29-9) → (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid (259212-61-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 3h; under 760.051 Torr;

DOI:10.1055/s-0030-1259527

Reference yield: 96.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid (259212-61-8)

Guidance literature:

tert-butylchlorodiphenylsilane; 4R-4-hydroxyproline; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; for 24h;

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 1.5h;

DOI:10.1039/c3ob27250h

Reference yield: 75.0%

tert-butyldiphenylsilane (33729-92-9) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid (259212-61-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; for 24h;

DOI:10.1021/jo200838v

upstream raw materials:

(2S,4R)-4-(tert-butyldiphenylsiloxy)pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

tert-butylchlorodiphenylsilane

4R-4-hydroxyproline

Downstream raw materials:

trans-4-tert-butyldiphenylsiloxy-N-Boc-L-proline carboxylic acid

di-tert-butyl 5,5′-(5,8-dioxa-2,11-diazadodecane-1,12-dioyl)-bis(3-((tert-butyldiphenylsilyl)oxy)pyrrolidine-1-carboxylate)

N,N′-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-((tertbutyldiphenylsilyl)oxy)pyrrolidine-2-carboxamide)

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