[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

Base Information

Chemical Name:[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran
CAS No.:440103-82-2
Molecular Formula:C₂₆H₄₈O₅SSi₂
Molecular Weight:528.901
Hs Code.:

Synonyms:[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

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Chemical Property of [2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

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Technology Process of [2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

There total 28 articles about [2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran 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%

: 440104-23-4
(2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 440103-82-2
[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -15 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1016/j.tet.2015.08.011

Reference yield:

: 440104-18-7
[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol

: 440103-82-2
[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

2.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

3.1: perchloric acid / tetrahydrofuran; H₂O / 2 h / Heating

3.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

4.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH₂Cl₂; decane / 29 h / 20 °C

5.1: sodium iodide; 18-c-6 / butan-2-one / Heating

5.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating

6.1: 93 percent / triethylamine / CH₂Cl₂ / 3 h / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 18-crown-6 ether; pyridinium p-toluenesulfonate; triethylamine; sodium iodide; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; water; butanone;
DOI:10.1021/ol025872f

Reference yield:

: 3-(6-benzenesulfonyl-4-methyl-hex-3-enyl)-3-methyl-oxiran-2-ylmethanol

: 440103-82-2
[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

2.1: perchloric acid / tetrahydrofuran; H₂O / 2 h / Heating

2.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

3.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH₂Cl₂; decane / 29 h / 20 °C

4.1: sodium iodide; 18-c-6 / butan-2-one / Heating

4.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating

5.1: 93 percent / triethylamine / CH₂Cl₂ / 3 h / -78 °C

With pyridine; tert.-butylhydroperoxide; perchloric acid; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; pyridinium p-toluenesulfonate; triethylamine; sodium iodide; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; water; butanone;
DOI:10.1021/ol025872f