[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Chemical Name:[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane
CAS No.:944823-58-9
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

There total 8 articles about [(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 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: 90.0%

: 856426-88-5
(S)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butan-1-ol

: 100-39-0
benzyl bromide

: 944823-58-9
[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: (S)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-butan-1-ol; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;
DOI:10.1016/j.tet.2007.02.039

Reference yield:

: 121422-51-3
(2S,3R)-3-hydroxy-2-vinyloxane

: 944823-58-9
[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / imidazole; DMAP / dimethylformamide / 5 h / 20 °C

2.1: OsO₄; NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 23 h / 20 °C

2.2: NaIO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 8 h / 20 °C

3.1: 1.44 g / CH₂Cl₂ / 12 h / 20 °C

4.1: 90 percent / TMSCl; bis(N-isopropylsalicylaldimine) copper(II) complex / tetrahydrofuran; diethyl ether / 1.5 h / -45 °C

5.1: 95 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -78 °C

6.1: KOt-Bu / tetrahydrofuran / 0.17 h / 20 °C

6.2: 90 percent / Bu₄NI / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; chloro-trimethyl-silane; N-methyl-2-indolinone; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Wittig reaction;
DOI:10.1016/j.tet.2007.02.039

Reference yield:

: 856426-85-2
(E)-3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

: 944823-58-9
[(2S,3R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / TMSCl; bis(N-isopropylsalicylaldimine) copper(II) complex / tetrahydrofuran; diethyl ether / 1.5 h / -45 °C

2.1: 95 percent / DIBALH / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: KOt-Bu / tetrahydrofuran / 0.17 h / 20 °C

3.2: 90 percent / Bu₄NI / tetrahydrofuran / 1 h / 20 °C

With chloro-trimethyl-silane; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/j.tet.2007.02.039