((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane
CAS No.:1269803-16-8
Molecular Formula:C₂₈H₅₀O₄Si
Molecular Weight:478.788
Hs Code.:

Synonyms:((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

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Chemical Property of ((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

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Technology Process of ((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

There total 21 articles about ((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane 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: 80.0%

: 1269803-27-1
C₂₀H₄₂O₃Si

: 2746-25-0
p-Methoxybenzyl bromide

: 1269803-16-8
((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

Guidance literature:: C₂₀H₄₂O₃Si; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1.16667h; Inert atmosphere;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1146690-87-0
(3S)-9-(benzyloxy)-3-(2-bromo-1-ethoxyethoxy)-1-nonyne

: 1269803-16-8
((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 14 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 0.5 h / Inert atmosphere; Reflux

2.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

3.1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

5.1: iodine / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / Inert atmosphere

7.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

7.2: 3 h / -20 - 0 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

8.2: 3 h / -78 °C / Inert atmosphere

9.1: lithium borohydride; water / diethyl ether / 0 °C

10.1: 1H-imidazole / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere

11.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C

12.1: sodium periodate / tetrahydrofuran; water / 1 h / 23 °C

13.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

14.1: sodium hydride / tetrahydrofuran / 1.17 h / 0 - 20 °C / Inert atmosphere

14.2: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Jones reagent; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; water; iodine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pivaloyl chloride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; benzene; 3.1: Jones oxidation;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1146690-68-7
(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

: 1269803-16-8
((S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexyloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

2.1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: iodine / dichloromethane / -78 - 20 °C / Inert atmosphere

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / Inert atmosphere

6.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

6.2: 3 h / -20 - 0 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 3 h / -78 °C / Inert atmosphere

8.1: lithium borohydride; water / diethyl ether / 0 °C

9.1: 1H-imidazole / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere

10.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 20 °C

11.1: sodium periodate / tetrahydrofuran; water / 1 h / 23 °C

12.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

13.1: sodium hydride / tetrahydrofuran / 1.17 h / 0 - 20 °C / Inert atmosphere

13.2: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Jones reagent; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; water; iodine; sodium hexamethyldisilazane; pivaloyl chloride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; 2.1: Jones oxidation;
DOI:10.1002/ejoc.201001205