Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate

Base Information

• Chemical Name: Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate
• CAS No.: 87729-38-2
• Molecular Formula: C12H26O3Si
• Molecular Weight: 246.41900
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60456685
• Wikidata: Q82279241
• Mol file: 87729-38-2.mol

Synonyms:87729-38-2;methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate;SCHEMBL839062;DTXSID60456685;OELKSEYIZGQEGQ-UHFFFAOYSA-N;5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-pentanoicacidmethylester

Chemical Property of Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate

Chemical Property:

• PSA: 35.53000
• LogP: 3.35150
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 246.16512122
• Heavy Atom Count: 16
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

5-[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]PENTANOIC ACIDMETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCCCCC(=O)OC

Technology Process of Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate

There total 4 articles about Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate 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: 80.0%

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + methanol (67-56-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilanyloxy)pentanoic acid methyl ester (87729-38-2)

Guidance literature:

3,4,5,6-tetrahydro-2H-pyran-2-one; methanol; With sulfuric acid; for 21h; Heating;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 21h;

DOI:10.1016/S0957-4166(03)00125-3

Reference yield: 68.0%

1H-imidazole (288-32-4) + methyl 5-hydroxypentanoate (14273-92-8) + ammonium chloride + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilanyloxy)pentanoic acid methyl ester (87729-38-2)

Guidance literature:

In N-methyl-acetamide;

Reference yield: 60.5%

methyl 5-hydroxypentanoate (14273-92-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilanyloxy)pentanoic acid methyl ester (87729-38-2)

Guidance literature:

With dmap; In dichloromethane; for 19h; Ambient temperature;

DOI:10.1021/jo00177a015

upstream raw materials:

methyl 5-hydroxypentanoate

tert-butyldimethylsilyl chloride

3,4,5,6-tetrahydro-2H-pyran-2-one

methanol

Downstream raw materials:

6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-one

(S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-ol

1-[(R)-(S)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexane-1-sulfinyl]-4-methyl-benzene

6-trans-Leukotriene B₄

Refernces

• 1、 Hanquet, Gilles,Salom-Roig, Xavier J.,Gressot-Kempf, Laurence,Lanners, Steve,Solladie, Guy. "New insights into the reduction of β,δ-diketo-sulfoxides". . p. 1291 - 1301. Retrieved 2007/10/03.
• 2、 Kraus, George A.,Thurston, Jeff. "ALKOXY RADICALS IN ORGANIC SYNTHESIS. A NOVEL APPROACH TO SPIROKETALS". . p. 4011 - 4014. Retrieved 2007/10/02.