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

Base Information

• Chemical Name: [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate
• CAS No.: 351412-73-2
• Molecular Formula: C₂₅H₄₄O₅SSi₂
• Molecular Weight: 512.858
• Mol file: 351412-73-2.mol

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

Chemical Property of [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate

There total 6 articles about [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-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: 93.0%

[(2R,3R)-2,3-dihydroxy-3-methylpent-4-ynyl](4-methylphenyl)sulfonate (351412-72-1) + t-butyldimethylsiyl triflate (69739-34-0) → [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate (351412-73-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja003956i

Reference yield:

(2R,3R)-3-methylpent-4-yne-1,2,3-triol (351412-71-0) → [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate (351412-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 19 percent / pyridine / toluene / 12 h / 20 °C

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

With pyridine; 2,6-dimethylpyridine; In dichloromethane; toluene;

DOI:10.1021/ja003956i

Reference yield:

(4R)-4-[(1S)-1-trimethylsilylethynyl(2-oxiranyl)]-2,2-dimethyl-1,3-dioxolane (351412-69-6) → [(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate (351412-73-2)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; L-Selectride; acetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja003956i

upstream raw materials:

[(2R,3R)-2,3-dihydroxy-3-methylpent-4-ynyl](4-methylphenyl)sulfonate

t-butyldimethylsiyl triflate

(2R,3R)-3-methylpent-4-yne-1,2,3-triol

(2R)-2-[(1R)-3,3-dimethyl(2,4-dioxolanyl)]-4-trimethylsilylbut-3-yn-2-ol

Downstream raw materials:

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