(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

Base Information

Chemical Name:(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol
CAS No.:624727-32-8
Molecular Formula:C₂₄H₄₄O₆Si
Molecular Weight:456.695
Hs Code.:

Synonyms:(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

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Chemical Property of (2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

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Technology Process of (2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

There total 8 articles about (2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol 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: 77.0%

: 624727-30-6
(4S)-4-benzyl-3-[(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptanoyl]-1,3-oxazolidin-2-one

: 624727-32-8
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 20 ℃;
DOI:10.1021/jo035054g

Reference yield:

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

: 624727-32-8
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

Guidance literature:: Multi-step reaction with 7 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

4: DIBAH / CH₂Cl₂; hexane / 3.5 h / -78 °C

5: 5.67 g / TiCl₄; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

6: 81 percent / (iPr)2NEt; tetrabutylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

7: 77 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; lithium borohydride; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; (-)-sparteine; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035054g

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 624727-32-8
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: ClCH₂CO₂H; aq. NaOH; acetic acid / 144 h / 40 °C

2: 80 percent / SnCl₂ / CH₂Cl₂ / 1 h / 20 °C

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

4: imidazole; DMAP / dimethylformamide / 48 h

5: DIBAH / CH₂Cl₂; hexane / 3.5 h / -78 °C

6: 5.67 g / TiCl₄; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

7: 81 percent / (iPr)2NEt; tetrabutylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

8: 77 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium borohydride; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; acetic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; chloroacetic acid; tin(ll) chloride; (-)-sparteine; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035054g