Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester
CAS No.:444200-20-8
Molecular Formula:C₃₅H₅₈O₈SSi
Molecular Weight:666.992
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

There total 7 articles about Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl 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:

: 119649-27-3
4-((4-methoxybenzyl)oxy)butanal

: 444200-20-8
Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium dicyclohexylamide / diethyl ether; hexane / 1 h / -78 °C

1.2: CpTiCl(O-diacetone-D-glucose)2 / diethyl ether; hexane / 2.5 h / -78 - -30 °C

1.3: 74 percent / diethyl ether; hexane / 2 h / -78 °C

2.1: 83 percent / imidazole; dimethylformamide / 72 h / 20 °C

3.1: 90 percent / DIBAH / CH₂Cl₂; hexane; methanol / 4 h / -78 - 20 °C

4.1: 90 percent / titanium(IV) chloride; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

5.1: 87 percent / N,N-diisopropylethylamine; tetrabutylammonium iodide / CH₂Cl₂ / 18 h / 20 °C

6.1: 90 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 - 20 °C

7.1: pyridine / 2 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; lithium dicyclohexylamide; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1.3: Duthaler aldol reaction;
DOI:10.1021/ol026040k

Reference yield:

: 444200-10-6
tert-butyl (3S)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate

: 444200-20-8
Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / imidazole; dimethylformamide / 72 h / 20 °C

2: 90 percent / DIBAH / CH₂Cl₂; hexane; methanol / 4 h / -78 - 20 °C

3: 90 percent / titanium(IV) chloride; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

4: 87 percent / N,N-diisopropylethylamine; tetrabutylammonium iodide / CH₂Cl₂ / 18 h / 20 °C

5: 90 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 - 20 °C

6: pyridine / 2 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; (-)-sparteine; In tetrahydrofuran; methanol; hexane; dichloromethane; water;
DOI:10.1021/ol026040k

Reference yield:

: 444200-11-7
(3S)-6-[(4-methoxybenzyl)oxy]-3-[(triisopropylsilyl)oxy]hexanal

: 444200-20-8
Toluene-4-sulfonic acid (2R,3R,5S)-8-(4-methoxy-benzyloxy)-3-methoxymethoxy-2-methyl-5-triisopropylsilanyloxy-octyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / titanium(IV) chloride; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

2: 87 percent / N,N-diisopropylethylamine; tetrabutylammonium iodide / CH₂Cl₂ / 18 h / 20 °C

3: 90 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 - 20 °C

4: pyridine / 2 h / 0 °C

With pyridine; sodium tetrahydroborate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; (-)-sparteine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol026040k