(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

Base Information

Chemical Name:(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol
CAS No.:1198616-14-6
Molecular Formula:C₃₄H₃₆O₄S
Molecular Weight:540.723
Hs Code.:

Synonyms:(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

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Chemical Property of (S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

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Technology Process of (S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

There total 5 articles about (S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol 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: 89.0%

: 1198616-13-5
(S(R),2R,4S)-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

: 77-76-9
2,2-dimethoxy-propane

: 1198616-14-6
(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

Guidance literature:: With triethylamine; toluene-4-sulfonic acid; In acetone;

Reference yield:

: (2R,4S)-4-((tert-butyldimethylsilyl)oxy)-1-((R)-p-tolylsulfinyl)-5-(trityloxy)pentan-2-ol

: 1198616-14-6
(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

2: toluene-4-sulfonic acid / acetone / 1 h / 20 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone;
DOI:10.3762/bjoc.17.99

Reference yield:

: 144754-24-5,113240-53-2
(S)-methyl 3-hydroxy-4-(trityloxy)butanoate

: 1198616-14-6
(S(R),2R,4S)-2,4-O-isopropylidene-1-(p-tolylsulfinyl)-5-(triphenylmethyloxy)pentane-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; 1H-imidazole / dichloromethane / 12 h / 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -40 - 20 °C / Inert atmosphere

3.1: zinc(II) chloride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.2: 2 h / -78 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetone;
DOI:10.3762/bjoc.17.99