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

Base Information

• Chemical Name: (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane
• CAS No.: 947696-73-3
• Molecular Formula: C₄₂H₇₆O₄Si₃
• Molecular Weight: 729.32
• Mol file: 947696-73-3.mol

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

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

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)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane

There total 16 articles about (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane 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: 84.0%

methyl trifluoromethanesulfonate (333-27-7) + (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol (947696-81-3) → (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane (947696-73-3)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In chloroform; for 4h; Heating;

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)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane (947696-73-3)

Guidance literature:

Multi-step reaction with 6 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

6.1: 84 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 2 h / Heating

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

DOI:10.1002/chem.200700342

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-2,6-dimethyl-heptanal → (2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane (947696-73-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 3.53 g / CH₂Cl₂ / 3 h / 0 °C

2.1: 90 percent / 2.6-lutidine / CH₂Cl₂ / 1 h / 20 °C

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

4.1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 2.49 g / CH₂Cl₂ / 20 °C

5.1: 70 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

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

7.1: 84 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 2 h / Heating

With 2,6-dimethylpyridine; lithium hydroxide; 2,6-di-tert-butyl-pyridine; dihydrogen peroxide; tri-n-butyl-tin hydride; dimethylaluminum chloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; 1.1: Evans asymmetric aldolization;

DOI:10.1002/chem.200700342

upstream raw materials:

methyl trifluoromethanesulfonate

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

(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