(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

Base Information

Chemical Name:(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one
CAS No.:884345-48-6
Molecular Formula:C₄₄H₇₄O₅Si₃
Molecular Weight:767.325
Hs Code.:

Synonyms:(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

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Chemical Property of (8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

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Technology Process of (8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

There total 10 articles about (8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-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:

: (3R,4R)-4-Hydroxy-3-(2-trimethylsilanyl-ethoxymethoxy)-pentanoic acid methoxy-methyl-amide

: 884345-48-6
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

Guidance literature:: Multi-step reaction with 10 steps

1: imidazole

2: 87 percent / DIBAL-H / tetrahydrofuran / -78 °C

3: Zn / -78 - -15 °C

4: PPh₃; DIAD / tetrahydrofuran

5: NaOH / methanol

6: 94 percent / 2,6-lutidine

7: 92 percent / nBuLi / -78 °C

8: 43 percent / Bu₃SnOMe / PdCl₂*dppe / toluene / 120 °C

9: 64 percent / MgBr₂; nBuSH; K₂CO₃

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; n-butanethiol; di-isopropyl azodicarboxylate; tributyltin methoxide; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; magnesium bromide; zinc; (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); In tetrahydrofuran; methanol; toluene; 4: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-42-0
(3R,4R)-4-tert-butyldimethylsilyloxy-3-(2-trimethylsilylethoxymethoxy)pentanoic acid methoxymethylamide

: 884345-48-6
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / DIBAL-H / tetrahydrofuran / -78 °C

2: Zn / -78 - -15 °C

3: PPh₃; DIAD / tetrahydrofuran

4: NaOH / methanol

5: 94 percent / 2,6-lutidine

6: 92 percent / nBuLi / -78 °C

7: 43 percent / Bu₃SnOMe / PdCl₂*dppe / toluene / 120 °C

8: 64 percent / MgBr₂; nBuSH; K₂CO₃

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; n-butanethiol; di-isopropyl azodicarboxylate; tributyltin methoxide; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; magnesium bromide; zinc; (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); In tetrahydrofuran; methanol; toluene; 3: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-43-1
(3R,4R)-4-tert-butyldimethylsilyloxy-3-(2-trimethylsilylethoxymethoxy)pentanal

: 884345-48-6
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tert-butyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-hydroxydodec-1-en-4-one

Guidance literature:: Multi-step reaction with 8 steps

1: Zn / -78 - -15 °C

2: PPh₃; DIAD / tetrahydrofuran

3: NaOH / methanol

4: 94 percent / 2,6-lutidine

5: 92 percent / nBuLi / -78 °C

6: 43 percent / Bu₃SnOMe / PdCl₂*dppe / toluene / 120 °C

7: 64 percent / MgBr₂; nBuSH; K₂CO₃

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; n-butanethiol; di-isopropyl azodicarboxylate; tributyltin methoxide; potassium carbonate; triphenylphosphine; magnesium bromide; zinc; (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); In tetrahydrofuran; methanol; toluene; 2: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2006.01.097