(2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol

Base Information

• Chemical Name: (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol
• CAS No.: 1391093-64-3
• Molecular Formula: C₁₉H₃₄O₃Si
• Molecular Weight: 338.563
• Mol file: 1391093-64-3.mol

Synonyms:(2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol

Chemical Property of (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol

There total 1 articles about (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-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: 86.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol (73814-98-9,73814-99-0,105560-79-0,143005-16-7) → (2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol (1391093-64-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.05.103

Reference yield: 71.0%

(2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol (1391093-64-3) + methyl iodide (74-88-4) → ((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane (1391093-66-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

(2R,3S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-2-methylpentan-3-ol (1391093-64-3) → (2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one (1391093-76-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

4.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

4.2: 0.33 h / 0 °C

4.3: 3 h / 0 °C

5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

6.1: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

7.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

7.2: 0.33 h / 0 °C

7.3: 12 h / 0 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; mineral oil;

DOI:10.1016/j.tetlet.2012.05.103

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol

Downstream raw materials:

(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

(2S,3R,4S,5R,6S,7S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-methoxy-2,4,6-trimethylnonan-1-one

((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane