Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester
CAS No.:179945-18-7
Molecular Formula:C₂₈H₄₄O₆SSi
Molecular Weight:536.805
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

There total 9 articles about Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl 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: 100.0%

: 98-59-9
p-toluenesulfonyl chloride

: 157220-46-7
(2R,3R,4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hexane-1,3-diol

: 179945-18-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

Guidance literature:: With pyridine; at 0 ℃; for 5h;
DOI:10.1021/jo9606113

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 179945-18-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 99 percent / trimethylaluminum / tetrahydrofuran; toluene; CH₂Cl₂ / 1.5 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

4: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

5: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

6: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

7: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

8: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

9: 100 percent / pyridine / 5 h / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; trimethylaluminum; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9606113

Reference yield:

: 179945-16-5
(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

: 179945-18-7
Toluene-4-sulfonic acid (2R,3R,4R,5S)-6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

2: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

3: 100 percent / pyridine / 5 h / 0 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; (+)-Weinsaeure-diethylester; In dichloromethane; toluene;
DOI:10.1021/jo9606113