Hexanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4-methoxyphenyl)methoxy]-, ethyl ester, (3R)-

Base Information

• Chemical Name: Hexanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4-methoxyphenyl)methoxy]-, ethyl ester, (3R)-
• CAS No.: 825612-51-9
• Molecular Formula: C22H38O5Si
• Molecular Weight: 410.626
• Mol file: 825612-51-9.mol

Synonyms:(R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-hexanoic acid ethyl ester;

Chemical Property of Hexanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4-methoxyphenyl)methoxy]-, ethyl ester, (3R)-

Chemical Property:

• PSA: 53.99000
• LogP: 5.33560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Hexanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4-methoxyphenyl)methoxy]-, ethyl ester, (3R)-

There total 1 articles about Hexanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4-methoxyphenyl)methoxy]-, ethyl ester, (3R)- 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%

ethyl (3RS)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate + t-butyldimethylsiyl triflate (69739-34-0) → ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanoate (825612-51-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 23 ℃;

DOI:10.1002/chem.200400617

Reference yield: 83.0%

ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanoate (825612-51-9) → (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal (825612-52-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1002/chem.200400617

Reference yield:

ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanoate (825612-51-9) → (-)-salicylihalamide A (198481-99-1,198482-00-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 83 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

2.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl₄ / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 78 percent / CH₂Cl₂ / 1 h / 0 °C

3.1: 86 percent / N,N-diisopropylethylamine; Bu₄NI / CH₂Cl₂ / 12 h / 0 - 23 °C

4.1: 80 percent / aq. NaBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

5.1: 100 percent / pyridine / 5 h / 0 °C

6.1: 89 percent / NaI; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dimethoxy-ethane / 3 h / Heating

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 - 23 °C

7.2: 84 percent / aq. NaOH / [PdCl₂(1,1'-bis(diphenylphosphanyl)ferrocene)] / 4 h / 40 °C

8.1: 100 percent / TBAF / tetrahydrofuran / 48 h / 0 °C

9.1: 72 percent / aq. LiOH / tetrahydrofuran; ethanol / 72 h / 70 °C

10.1: polystyrene-bound PPh₃ / tetrahydrofuran / 0.25 h / 23 °C

10.2: 72 percent / DEAD / toluene / 24 h / 0 - 20 °C

11.1: 52 percent / 9-I-9-BBN / hexane; CH₂Cl₂ / 0.03 h

12.1: 60 percent / DMAP; imidazole / dimethylformamide / 96 h / 23 °C

13.1: 85 percent / (+/-)-camphorsulfonic acid / CH₂Cl₂; methanol / 1.5 h / 0 °C

14.1: 91 percent / 4-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 0 °C

15.1: DIBAL / hexane; tetrahydrofuran / 0.5 h / 0 °C

15.2: 61 percent / hexane; tetrahydrofuran / 14 h / 0 °C

16.1: 45 percent / pyridine; Ac₂O / tetrahydrofuran / 72 h

17.1: 75 percent / HF*pyridine / tetrahydrofuran / 72 h / 23 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; polystyrene-bound PPh₃; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic anhydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; sodium iodide; 9-iodo-9-borabicyclo{3.3.1}nonane; titanium tetrachloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 7.2: Suzuki cross-coupling / 10.1: Mitsunobu reaction;

DOI:10.1002/chem.200400617

upstream raw materials:

t-butyldimethylsiyl triflate

Downstream raw materials:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal

(4R,6R,7S)-1-[(4-methoxybenzyl)oxy]-6(methoxymethoxy)-7-methyl-9-decen-4-ol

(4R,6R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-7-methyloct-7-ene

(2R,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methyl-1-octanol

Refernces