(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

Base Information

Chemical Name:(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate
CAS No.:826995-02-2
Molecular Formula:C₂₇H₃₇BrO₄Si
Molecular Weight:533.578
Hs Code.:

Synonyms:(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

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Chemical Property of (2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

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Technology Process of (2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

There total 1 articles about (2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate 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: 58.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

: tert-butyl{2-[(2S)-5-methyl-5-propyl-2,5-dihydrofuran-2-yl]ethoxy}diphenylsilane

: 826994-89-2
(2S,3S,4R,5R)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

: 826995-02-2
(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

Guidance literature:: With N-Bromosuccinimide; water; at -5 ℃; for 6h;
DOI:10.1021/ja044130+

Reference yield:

: 826995-02-2
(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

: (E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5S)-3-(4-methoxy-benzoyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: (TMS)3SiH; AIBN / toluene / 4 h / 80 °C

2.1: NaHCO₃ / methanol; H₂O / 2 h

3.1: 54 percent / PPTS / CH₂Cl₂; cyclohexane / 48 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 3 h

5.1: 89 percent / PPh₃; imidazole; iodine / diethyl ether; acetonitrile / 2 h

6.1: tert-BuLi / pentane; diethyl ether; tetrahydrofuran / 0.08 h / -78 °C

6.2: pentane; diethyl ether; tetrahydrofuran / 1.25 h

7.1: K₃PO₄; AsPh₃ / (dppf)PdCl₂ / tetrahydrofuran; H₂O; dimethylformamide / 2 h

With 1H-imidazole; potassium phosphate; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triphenylphosphine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 7.1: Suzuki coupling;
DOI:10.1021/ja061918e

Reference yield:

: 826995-02-2
(2S,3S,4R,5S)-4-bromo-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-methyl-5-propyltetrahydrofuran-3-yl formate

: (E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5S)-3-(4-methoxy-benzoyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: (TMS)3SiH; AIBN / toluene / 4 h / 80 °C

2.1: NaHCO₃ / methanol; H₂O / 2 h

3.1: 54 percent / PPTS / CH₂Cl₂; cyclohexane / 48 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 3 h

5.1: 89 percent / PPh₃; imidazole; iodine / diethyl ether; acetonitrile / 2 h

6.1: tert-BuLi / pentane; diethyl ether; tetrahydrofuran / 0.08 h / -78 °C

6.2: pentane; diethyl ether; tetrahydrofuran / 1.25 h

7.1: K₃PO₄; AsPh₃ / (dppf)PdCl₂ / tetrahydrofuran; H₂O; dimethylformamide / 2 h

8.1: LiI; pyridine / 30 h / 125 °C

With pyridine; 1H-imidazole; potassium phosphate; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triphenylphosphine; lithium iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 7.1: Suzuki coupling;
DOI:10.1021/ja061918e