(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Base Information

Chemical Name:(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
CAS No.:861807-65-0
Molecular Formula:C₂₅H₃₉IO₃SSi
Molecular Weight:574.639
Hs Code.:

Synonyms:(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

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Chemical Property of (2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

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Technology Process of (2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

There total 16 articles about (2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 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: 16.0%

: 861807-64-9
(2R)-2-(tert-butyldimethylsilyl)oxy-1,8-diiodooct-7-ene

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 861807-65-0
(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2005.04.144

Reference yield:

: 85807-84-7
tert-butyl(5-hexenyloxy)dimethylsilane

: 861807-65-0
(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: (DHQD)2AQN; methanesulfonamide; K₂CO₃ / K₃Fe(CN)6; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 26 h / 0 °C

2.1: p-toluenesulfonic acid / 0.5 h

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 19 h / 20 °C

4.1: triethylamine / CH₂Cl₂ / 0.17 h / -5 °C

5.1: 5.07 g / NaI; NaHCO₃ / acetone / 18 h / 20 °C

6.1: dimethylsulfoxide / 18 h / 20 °C

7.1: n-Bu₃SnH; 2,2'-azobisisobutyronitrile / 3 h / 120 °C

7.2: iodine / tetrahydrofuran / 1 h / 0 °C

8.1: hydrochloric acid / methanol / 2 h / 20 °C

9.1: pyridine / 15 h / 20 °C

10.1: NaH / tetrahydrofuran / 19 h / 20 °C

11.1: LiI; AcOH / tetrahydrofuran; H₂O / 1 h / 0 °C

12.1: imidazole / dimethylformamide / 15 h

13.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h

13.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / 1 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; hydroquinidine anthraquinone-1,4-diyl diether; 2,2'-azobis(isobutyronitrile); methanesulfonamide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; lithium iodide; lithium diisopropyl amide; potassium osmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.bmc.2005.12.015

Reference yield:

: 821-41-0
5-Hexen-1-ol

: 861807-65-0
(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 89 percent / imidazole / dimethylformamide

2.1: (DHQD)2AQN; methanesulfonamide; K₂CO₃ / K₃Fe(CN)6; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 26 h / 0 °C

3.1: p-toluenesulfonic acid / 0.5 h

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 19 h / 20 °C

5.1: triethylamine / CH₂Cl₂ / 0.17 h / -5 °C

6.1: 5.07 g / NaI; NaHCO₃ / acetone / 18 h / 20 °C

7.1: dimethylsulfoxide / 18 h / 20 °C

8.1: n-Bu₃SnH; 2,2'-azobisisobutyronitrile / 3 h / 120 °C

8.2: iodine / tetrahydrofuran / 1 h / 0 °C

9.1: hydrochloric acid / methanol / 2 h / 20 °C

10.1: pyridine / 15 h / 20 °C

11.1: NaH / tetrahydrofuran / 19 h / 20 °C

12.1: LiI; AcOH / tetrahydrofuran; H₂O / 1 h / 0 °C

13.1: imidazole / dimethylformamide / 15 h

14.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h

14.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / 1 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; hydroquinidine anthraquinone-1,4-diyl diether; 2,2'-azobis(isobutyronitrile); methanesulfonamide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; lithium iodide; lithium diisopropyl amide; potassium osmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.bmc.2005.12.015