(2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol

Base Information

• Chemical Name: (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol
• CAS No.: 947696-81-3
• Molecular Formula: C₄₁H₇₄O₄Si₃
• Molecular Weight: 715.293

Synonyms:(2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol

Chemical Property of (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol

There total 15 articles about (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-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:

(3S,4R,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-one (947696-74-4) → (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol (947696-81-3) + (2R,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol

Guidance literature:

With tri-n-butyl-tin hydride; dimethylaluminum chloride; In dichloromethane; at -90 ℃; for 1h; Title compound not separated from byproducts.;

DOI:10.1016/j.tetlet.2004.08.013

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol (947696-81-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / 2.6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: aq. H₂O₂; LiOH monohydrate / tetrahydrofuran / 0 - 20 °C

3.1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 2.49 g / CH₂Cl₂ / 20 °C

4.1: 70 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

5.1: Me₂AlCl; n-Bu₃SnH / CH₂Cl₂ / 1 h / -90 °C

With 2,6-dimethylpyridine; lithium hydroxide; dihydrogen peroxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/chem.200700342

Reference yield:

(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide (947696-76-6) → (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol (947696-81-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 3.53 g / CH₂Cl₂ / 3 h / 0 °C

4.1: 90 percent / 2.6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5.1: aq. H₂O₂; LiOH monohydrate / tetrahydrofuran / 0 - 20 °C

6.1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 2.49 g / CH₂Cl₂ / 20 °C

7.1: 70 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

8.1: Me₂AlCl; n-Bu₃SnH / CH₂Cl₂ / 1 h / -90 °C

With 2,6-dimethylpyridine; lithium hydroxide; dihydrogen peroxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; diisobutylaluminium hydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.1: Evans asymmetric aldolization;

DOI:10.1002/chem.200700342

upstream raw materials:

(3S,4R,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-one

(4S)-4-benzyl-3-[(2S,3R,4S,5S,8S)-5-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one

(4S)-4-benzyl-3-[(2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one

(4R,5S)-4-methyl-5-phenyl-3-[(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one

Downstream raw materials:

(2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane

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