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

Base Information

Chemical Name:(2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol
CAS No.:440104-23-4
Molecular Formula:C₂₃H₄₀O₅SSi
Molecular Weight:456.719
Hs Code.:

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

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Chemical Property of (2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol

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Technology Process of (2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol

There total 27 articles about (2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-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: 97.0%

: 3112-85-4
methylphenylsulfonate

: tert-butyldimethyl[(1R)-1-[(2S,5R)-2-methyl-5-[(2S)-2-methyloxiran-2-yl]oxolan-2-yl]ethoxy]silane

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

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; Petroleum ether; at -78 - 20 ℃; for 4.66667h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2015.08.011

Reference yield: 81.0%

: 5-[3-benzenesulfonyl-1-hydroxy-1-methyl-propyl]-2-[1-(t-butyldimethylsiloxy)-2-p-toluenesulfonyloxy-ethyl]-2-methyl-tetrahydrofuran

: (S)-4-Benzenesulfonyl-2-{(2S,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-butan-2-ol

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

Guidance literature:: 5-[3-benzenesulfonyl-1-hydroxy-1-methyl-propyl]-2-[1-(t-butyldimethylsiloxy)-2-p-toluenesulfonyloxy-ethyl]-2-methyl-tetrahydrofuran; With 18-crown-6 ether; sodium iodide; In butanone; Heating;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 3h; Heating;
DOI:10.1021/ol025872f

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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