[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

Base Information

Chemical Name:[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate
CAS No.:351412-74-3
Molecular Formula:C₄₂H₆₆O₇SSi₃
Molecular Weight:799.304
Hs Code.:

[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

Synonyms:[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

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Chemical Property of [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

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Technology Process of [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

There total 7 articles about [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate 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: 48.0%

: 351412-73-2
[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate

: 1-tert-butyldimethylsilyloxy-2-naphthoaldehyde

: 351412-74-3
[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

Guidance literature:: [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate; With cerium(III) chloride; In tetrahydrofuran; at 20 ℃; for 0.833333h;

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

1-tert-butyldimethylsilyloxy-2-naphthoaldehyde; In tetrahydrofuran; at -78 ℃; for 5h; Further stages.;
DOI:10.1021/ja003956i

Reference yield:

: 351412-71-0
(2R,3R)-3-methylpent-4-yne-1,2,3-triol

: 351412-74-3
[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 19 percent / pyridine / toluene / 12 h / 20 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3.1: CeCl₃ / tetrahydrofuran / 0.83 h / 20 °C

3.2: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.3: 48 percent / tetrahydrofuran / 5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; cerium(III) chloride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja003956i

Reference yield:

: 351412-69-6
(4R)-4-[(1S)-1-trimethylsilylethynyl(2-oxiranyl)]-2,2-dimethyl-1,3-dioxolane

: 351412-74-3
[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / L-selectride / tetrahydrofuran / 3 h / 0 °C

2.1: TBAF; acetic acid / tetrahydrofuran / 1 h / 0 °C

2.2: HCl / tetrahydrofuran; H₂O / 24 h / 20 °C

3.1: 19 percent / pyridine / toluene / 12 h / 20 °C

4.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

5.1: CeCl₃ / tetrahydrofuran / 0.83 h / 20 °C

5.2: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.3: 48 percent / tetrahydrofuran / 5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; cerium(III) chloride; tetrabutyl ammonium fluoride; L-Selectride; acetic acid; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja003956i