ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

Base Information

Chemical Name:ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate
CAS No.:624727-28-2
Molecular Formula:C₂₁H₃₆O₅Si
Molecular Weight:396.599
Hs Code.:

Synonyms:ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

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Chemical Property of ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

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Technology Process of ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

There total 4 articles about ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate 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: 93.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 624727-27-1
(+)-(R)-ethyl 5-(4-methoxybenzyloxy)-3-hydroxypentanoate

: 624727-28-2
ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/jo0701942

Reference yield:

: 624727-26-0
ethyl 5-[(4-methoxybenzyl)oxy]-3-oxopentanoate

: 624727-28-2
ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / (R)-BINAP; hydrogen / [RuCl₂(C₆H₆)]2 / dimethylformamide; ethanol / 62 h / 20 °C / 15001.5 Torr

2: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; dichloro(benzene)ruthenium(II) dimer; In ethanol; N,N-dimethyl-formamide; 1: asymmetric Noyori hydrogenation;
DOI:10.1021/jo0701942

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 624727-28-2
ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / SnCl₂ / CH₂Cl₂ / 1 h / 20 °C

2: H₂; (R)-(+)-BINAP / [RuCl₂(PhH)]2 / dimethylformamide / 20 h / 90 °C / 3000.24 Torr

3: imidazole; DMAP / dimethylformamide / 48 h

With 1H-imidazole; dmap; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; tin(ll) chloride; dichloro(benzene)ruthenium(II) dimer; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035054g