(2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol

Base Information

• Chemical Name: (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol
• CAS No.: 82849-08-9
• Molecular Formula: C₃₅H₆₈O₇Si₂
• Molecular Weight: 657.092

Synonyms:(2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol

Chemical Property of (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol

There total 4 articles about (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol 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:

(2S,3S,4R,6S,7R,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecan-5-one (82849-07-8) → (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol (82849-08-9)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃;

DOI:10.1021/ja00384a063

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol (82849-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

3: diisobutylaluminium hydride / diethyl ether / -78 °C

With 2,6-dimethylpyridine; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00384a063

Reference yield:

(4S,5R,6S,7S)-9-Benzyloxy-5-hydroxy-7-methoxy-4,6-dimethyl-nonan-3-one (82849-05-6) → (2S,3S,4R,5R,6R,7S,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecane-3,5-diol (82849-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: lithium 1,1,3,3-tetramethyl-1,3-diphenyldisilazide, bis(cyclopentadienyl)zirconium dichloride / tetrahydrofuran / -40 deg C -> -20 deg C

3: diisobutylaluminium hydride / diethyl ether / -78 °C

With 2,6-dimethylpyridine; zirconocene dichloride; lithium bis(dimethylphenylsilyl)amide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00384a063

upstream raw materials:

(2S,3S,4R,6S,7R,8R,9S)-11-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-undecan-5-one

t-butyldimethylsiyl triflate

(4S,5R,6S,7S)-9-Benzyloxy-5-hydroxy-7-methoxy-4,6-dimethyl-nonan-3-one

(4S,5R,6R,7S)-9-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-4,6-dimethyl-nonan-3-one

Downstream raw materials:

(4R,5R,6S)-4-[(1R,2R,3R,4S)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,3-dimethyl-hexyl]-2,2,5-trimethyl-6-[(S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-[1,3]dioxane

Trifluoro-acetic acid (1R,2R,3S)-3-methoxy-2-methyl-5-(toluene-4-sulfonyloxy)-1-((R)-1-{(4R,5R,6S)-2,2,5-trimethyl-6-[(S)-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-[1,3]dioxan-4-yl}-ethyl)-pentyl ester

(S)-6-[(4S,5R,6R)-6-((1R,2R,3R,4S)-6-Benzyloxy-4-methoxy-1,3-dimethyl-2-trimethylsilanyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-hydroxy-2-methyl-3-oxo-heptanoic acid benzyl ester

(R)-2-[(4R,5S,6R)-6-((1R,2R,3R,4S)-6-Benzyloxy-4-methoxy-1,3-dimethyl-2-trimethylsilanyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propionaldehyde

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