(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

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Chemical Name:(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol
CAS No.:1352577-31-1
Molecular Formula:C₃₄H₅₂O₅Si₂
Molecular Weight:596.955
Hs Code.:

Synonyms:(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

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Chemical Property of (S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

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Technology Process of (S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

There total 6 articles about (S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol 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: 92.0%

: 1352577-09-3
(2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-carbaldehyde

: 88158-68-3
4-(tert-butyldiphenylsilyloxy)-1-butyne

: 1352577-31-1
(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

Guidance literature:: 4-(tert-butyldiphenylsilyloxy)-1-butyne; With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 23 ℃; for 0.25h; Inert atmosphere;

(2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-carbaldehyde; In toluene; at 23 ℃; for 18h; Inert atmosphere;

With water; ammonium chloride; In toluene; at 23 ℃; for 0.0833333h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1072451-45-6
(S)-methyl 2-hydroxy-2-methylpent-4-enoate

: 1352577-31-1
(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

1.2: 19 h / -78 - 23 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / toluene / 2.75 h / 23 °C / Inert atmosphere

2.2: 0.17 h / 23 °C / Inert atmosphere

2.3: 14.5 h / 108 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / 3 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / diethyl ether; hexane / 0.58 h / -78 °C / Inert atmosphere

5.2: 15 h / -78 - 23 °C / Inert atmosphere

6.1: (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 23 °C / Inert atmosphere

6.2: 18 h / 23 °C / Inert atmosphere

6.3: 0.08 h / 23 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; (1S,2R)-(+)-N-methylephedrine; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1352577-28-6
(S)-methyl 2-methyl-3,4-dihydro-2H-pyran-2-carboxylate

: 1352577-31-1
(S)-1-(2S,5R,6R-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / 3 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 60 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / diethyl ether; hexane / 0.58 h / -78 °C / Inert atmosphere

3.2: 15 h / -78 - 23 °C / Inert atmosphere

4.1: (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 23 °C / Inert atmosphere

4.2: 18 h / 23 °C / Inert atmosphere

4.3: 0.08 h / 23 °C / Inert atmosphere

With 1H-imidazole; (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2011.09.079