Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester

Base Information

• Chemical Name: Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester
• CAS No.: 146830-59-3
• Molecular Formula: C23H32O3Si
• Molecular Weight: 384.591
• DSSTox Substance ID: DTXSID50439821
• Wikidata: Q82255910
• Mol file: 146830-59-3.mol

Synonyms:146830-59-3;Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester;DTXSID50439821

Chemical Property of Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 384.21207141
• Heavy Atom Count: 27
• Complexity: 413

Purity/Quality:

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)OCCCCCC(=O)OC

Technology Process of Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, methyl ester

There total 4 articles about Hexanoic acid, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, 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: 98.0%

methyl 6-hydroxycaproate (4547-43-7) + tert-butylchlorodiphenylsilane (58479-61-1) → 6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid methyl ester (146830-59-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jo00060a038

Reference yield: 50.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + tert-butyl-(5-iodo-pentyloxy)-diphenyl-silane (164025-54-1) → 6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid methyl ester (146830-59-3)

Guidance literature:

With indium; copper(I) triflate; In 1,4-dioxane; at 25 ℃; for 24h; under 760.051 Torr; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01573

Reference yield:

hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) → 6-((1,1-dimethylethyl)diphenylsilyloxy)hexanoic acid methyl ester (146830-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / methanol / Heating

2: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

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

DOI:10.1021/jo00060a038

upstream raw materials:

methyl 6-hydroxycaproate

tert-butylchlorodiphenylsilane

hexahydro-2H-oxepin-2-one

methanol

Downstream raw materials:

(+)<(S)R,2S>-1-(p-Tolylsulfinyl)-7-<(tert-butyldiphenylsilyl)oxy>-2-heptanol

(+)(6S)-10-(4-Hydroxy-3-methoxyhenyl)-8,8-(1,3-propanediyldithio)-6-hydroxy-1-<(tert-butyldiphenylsilyl)oxy>decane

Refernces

• 1、 Cui, Jin,Kawatake, Satoshi,Umegawa, Yuichi,Lethu, Sbastien,Yamagami, Masaki,Matsuoka, Shigeru,Sato, Fuminori,Matsumori, Nobuaki,Murata, Michio. "Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions". supporting information. p. 10279 - 10284. Retrieved 2015/10/28.
• 2、 Kobayashi, Yuichi,Motoyama, Yuuya. "Construction of the key amino alcohol moiety of the cinchona alkaloids". . p. 2670 - 2672. Retrieved 2008/09/16.