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

Base Information

Chemical Name:(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptyl 4-methylbenzenesulfonate
CAS No.:624727-34-0
Molecular Formula:C₃₁H₅₀O₈SSi
Molecular Weight:610.885
Hs Code.:

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

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

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

There total 9 articles about (2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptyl 4-methylbenzenesulfonate 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%

: 98-59-9
p-toluenesulfonyl chloride

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

: 624727-34-0
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptyl 4-methylbenzenesulfonate

Guidance literature:: With pyridine; at 0 ℃; for 2h;
DOI:10.1021/jo035054g

Reference yield:

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

: 624727-34-0
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 8 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

8: 98 percent / pyridine / 2 h / 0 °C

With pyridine; 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

: 624727-34-0
(2S,3R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-7-[(4-methoxybenzyl)oxy]-3-(methoxymethoxy)-2-methylheptyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 9 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

9: 98 percent / pyridine / 2 h / 0 °C

With pyridine; 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