(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

Base Information

Chemical Name:(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran
CAS No.:473535-41-0
Molecular Formula:C₂₉H₃₈O₃Si
Molecular Weight:462.704
Hs Code.:

Synonyms:(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

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Chemical Property of (2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

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Technology Process of (2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

There total 8 articles about (2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 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: 73.0%

: 563-47-3
3-Chloro-2-methylpropene

: (αR,2R,5S)-α-ethynyl-α-methyl-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-methanol

: 473535-41-0
(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

Guidance literature:: With n-butyllithium; lithium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 0 - 21 ℃; for 96h;
DOI:10.1021/jo016246j

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 473535-41-0
(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: imidazole

2.1: diisobutylaluminium hydride / CH₂Cl₂ / 2 h / -78 °C

3.1: triethylamine; DMAP / CH₂Cl₂ / 3 h

4.1: 1.70 g / tin(IV) chloride / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 83 percent / diethyl ether / 6 h / 0 °C

6.1: n-butyllithium; triethylamine / diethyl ether; hexane / 0.5 h / -78 °C

6.2: 25 mg / anhydrous cerium(III) chloride; triethylamine / diethyl ether; hexane / 2 h / -78 °C

7.1: 73 percent / anhydrous lithium iodide; n-butyllithium / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 96 h / 0 - 21 °C

With 1H-imidazole; dmap; n-butyllithium; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; lithium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; 6.2: Cram chelation-controlled addition;
DOI:10.1021/jo016246j

Reference yield:

: 21461-84-7
(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

: 473535-41-0
(2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 8 steps

1.1: BH₃-DMS

2.1: imidazole

3.1: diisobutylaluminium hydride / CH₂Cl₂ / 2 h / -78 °C

4.1: triethylamine; DMAP / CH₂Cl₂ / 3 h

5.1: 1.70 g / tin(IV) chloride / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 83 percent / diethyl ether / 6 h / 0 °C

7.1: n-butyllithium; triethylamine / diethyl ether; hexane / 0.5 h / -78 °C

7.2: 25 mg / anhydrous cerium(III) chloride; triethylamine / diethyl ether; hexane / 2 h / -78 °C

8.1: 73 percent / anhydrous lithium iodide; n-butyllithium / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 96 h / 0 - 21 °C

With 1H-imidazole; dmap; n-butyllithium; dimethylsulfide borane complex; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; lithium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; 7.2: Cram chelation-controlled addition;
DOI:10.1021/jo016246j