6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

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Chemical Name:6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one
CAS No.:473535-46-5
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

Synonyms:6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

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Chemical Property of 6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

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Technology Process of 6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

There total 13 articles about 6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-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: 100.0%

: 473535-45-4
(6R)-6-methyl-6-[(2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyloxy]methyl)tetrahydrofuran-2-yl]pyran-2[3H]-one

: 473535-46-5
6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 0.416667h;
DOI:10.1021/jo016246j

Reference yield:

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

: 473535-46-5
6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

Guidance literature:: Multi-step reaction with 13 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

8.1: ozone; Sudan Red / diethyl ether; methanol / -78 °C

8.2: 98 percent / dimethyl sulfide / diethyl ether; methanol / 6 h / -78 - 21 °C

9.1: 89 percent / hydrogen; quinoline / 5percent Pd-CaCO₃-Pb / methanol / 0.25 h

10.1: ozone / diethyl ether; methanol / 0.02 h / -78 °C

10.2: dimethyl sulfide / diethyl ether; methanol / 12 h / -78 - 21 °C

11.1: 18-crown-6; potassium carbonate / methanol / 2.5 h

12.1: 435 mg / DMAP; triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 3 h / 0 - 21 °C

13.1: 100 percent / hydrogen / Pd/C / methanol / 0.42 h

With 1H-imidazole; quinoline; dmap; n-butyllithium; 18-crown-6 ether; sudan red; hydrogen; tin(IV) chloride; diisobutylaluminium hydride; potassium carbonate; ozone; methanesulfonyl chloride; triethylamine; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; 6.2: Cram chelation-controlled addition / 9.1: Lindlar reduction;
DOI:10.1021/jo016246j

Reference yield:

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

: 473535-46-5
6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one

Guidance literature:: Multi-step reaction with 14 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

9.1: ozone; Sudan Red / diethyl ether; methanol / -78 °C

9.2: 98 percent / dimethyl sulfide / diethyl ether; methanol / 6 h / -78 - 21 °C

10.1: 89 percent / hydrogen; quinoline / 5percent Pd-CaCO₃-Pb / methanol / 0.25 h

11.1: ozone / diethyl ether; methanol / 0.02 h / -78 °C

11.2: dimethyl sulfide / diethyl ether; methanol / 12 h / -78 - 21 °C

12.1: 18-crown-6; potassium carbonate / methanol / 2.5 h

13.1: 435 mg / DMAP; triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 3 h / 0 - 21 °C

14.1: 100 percent / hydrogen / Pd/C / methanol / 0.42 h

With 1H-imidazole; quinoline; dmap; n-butyllithium; 18-crown-6 ether; dimethylsulfide borane complex; sudan red; hydrogen; tin(IV) chloride; diisobutylaluminium hydride; potassium carbonate; ozone; methanesulfonyl chloride; triethylamine; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; 7.2: Cram chelation-controlled addition / 10.1: Lindlar reduction;
DOI:10.1021/jo016246j