Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

Base Information

• Chemical Name: Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate
• CAS No.: 106513-42-2
• Molecular Formula: C₁₁H₂₄O₃Si
• Molecular Weight: 232.395
• DSSTox Substance ID: DTXSID80450140
• Nikkaji Number: J1.129.181C
• Wikidata: Q82269729
• Mol file: 106513-42-2.mol

Synonyms:106513-42-2;Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate;(S)-Ethyl 2-((tert-butyldimethylsilyl)oxy)propanoate;ethyl (2S)-2-[tert-butyl(dimethyl)silyl]oxypropanoate;Ethyl (S)-()-2-(tert-butyldimethylsilyloxy)propionate;MFCD00192135;SCHEMBL1578905;DTXSID80450140;TQP0256;KOBAXFIJEBLKRZ-VIFPVBQESA-N;AKOS015894003;BS-49927;CS-0188009;F52839;(S)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate;ethyl (S)-2-(tert-butyldimethylsilyloxy)propionate;(S)-2-((tert-butyldimethylsilyl)oxy)propanoic acid;(S)-Ethyl2-((tert-butyldimethylsilyl)oxy)propanoate;J-001603;Ethyl(S)-(-)-2-(tert-butyldimethylsilyloxy)propionate;(S)-(-)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate;(S)-2-(tert-Butyldimethylsiloxy)propanoic acid ethyl ester;(S)-2-(tert-butyl-dimethylsilanyloxy)propionic acid ethyl ester;Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate, 98%;(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propionic acid ethyl ester

Chemical Property of Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

Chemical Property:

• Vapor Pressure: 0.063mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 231.3°Cat760mmHg
• Flash Point: 78°C
• PSA: 35.53000
• Density: 0.907g/cm³
• LogP: 2.95980
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 232.14947116
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-Ethyl2-((tert-Butyldimethylsilyl)oxy)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C
• Uses: Precursor to the lactyl-3,4-didehydroproline didemnin B side chain. Starting material for the asymmetric synthesis of syn- and anti- functionalized1,2-diols.

Technology Process of Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

There total 5 articles about Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate 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%

(S)-Ethyl lactate (687-47-8) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate (105198-38-7,106513-42-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1039/c39860000393

Reference yield: 100.0%

(S)-Ethyl lactate (687-47-8) → ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate (105198-38-7,106513-42-2)

Guidance literature:

With 1H-imidazole; tert-butyldimethylsilyl chloride; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1021/jo501134d

Reference yield: 95.0%

ethanol (64-17-5) + (2S)-2-<(tert-Butyldimethylsilyl)oxy>lactic acid (129919-88-6) → ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate (105198-38-7,106513-42-2)

Guidance literature:

(2S)-2-<(tert-Butyldimethylsilyl)oxy>lactic acid; With trichloroisocyanuric acid; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.75h;

ethanol; With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.06.127

upstream raw materials:

(S)-Ethyl lactate

tert-butyldimethylsilyl chloride

ethanol

(2S)-2-<(tert-Butyldimethylsilyl)oxy>lactic acid

Downstream raw materials:

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-butan-2-one

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-thiopropionic acid S-phenyl ester

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

tert-Butyl-[(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-4-ynyloxy]-dimethyl-silane

Refernces

• 1、 -. "SHP2 INHIBITORS AND USES THEREOF". Page/Page column 133; 134. . Retrieved 2021/04/02.
• 2、 -. "PYRIMIDINE-FUSED CYCLIC COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF". Paragraph 0313; 0380-0382; 0886-0888. . Retrieved 2021/02/26.