(2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one

Base Information

• Chemical Name: (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one
• CAS No.: 858666-85-0
• Molecular Formula: C₄₇H₇₆O₅Si₃
• Molecular Weight: 805.374

Synonyms:(2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one

Chemical Property of (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one

There total 14 articles about (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one 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: 88.0%

4-benzenesulfonyl-1-benzyloxy-2,9-bis-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-10-methyl-undecan-5-one (858666-83-8) → (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one (858666-85-0)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol;

DOI:10.1021/ol0507975

Reference yield:

(2S,3S)-(+)-7-benzyloxy-1-tert-butyldiphenylsilyloxy-3-tert-butyldimethylsilyloxy-2-methylheptane (858666-78-1) → (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one (858666-85-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / H₂ / Pd/C / methanol

2.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

4.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

With pyridine; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; hydrogen; potassium carbonate; Dess-Martin periodane; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1039/b600951d

Reference yield:

(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one (858666-74-7) → (2S,9S,10S)-(-)-1-benzyloxy-2,9-bis-(tert-butyldimethylsilyloxy)-11-(tert-butyldiphenylsilyloxy)-10-methylundecane-5-one (858666-85-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / LiBH₄ / tetrahydrofuran / 0.08 h / 20 °C

2.1: 77 percent / imidazole / CH₂Cl₂ / 20 h / 20 °C

3.1: 95 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / dimethylformamide / 20 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / methanol

5.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

7.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

8.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; hydrogen; potassium carbonate; Dess-Martin periodane; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b600951d

upstream raw materials:

4-benzenesulfonyl-1-benzyloxy-2,9-bis-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-10-methyl-undecan-5-one

(S)-(-)-[4-benzyloxy-3-(tert-butyldimethylsilyloxy)butane]-1-sulfonylbenzene

(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-al

Downstream raw materials:

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-formyl-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

(1'E,2S,5R,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(3'-hydroxy-1'-propenyl)-1,6-dioxaspiro[4.5]decane

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