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

Base Information

Chemical Name:(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-1-en-4-one
CAS No.:884345-47-5
Molecular Formula:C₅₀H₈₈O₆Si₄
Molecular Weight:897.587
Hs Code.:

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

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

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

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

There total 26 articles about (8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-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: 43.0%

: 3,3-dimethyl-2-acetoxypenta-1,4-diene

: 884345-46-4
(2E,5R,7R,8R)-3-bromo-1-tert-butyldiphenylsilyloxy-5,8-bis-(tertbutyldimethylsilyloxy)-7-(2-trimethylsilylethoxymethoxy)non-2-ene

: (8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-4-en-2-one

: 884345-47-5
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-1-en-4-one

Guidance literature:: With tributyltin methoxide; (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); In toluene; at 120 ℃;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

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

: 884345-47-5
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-1-en-4-one

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; di-isopropyl azodicarboxylate; tributyltin methoxide; diisobutylaluminium hydride; triphenylphosphine; 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

: 884345-47-5
(8S,10R,11R)-8,11-bis-(tert-butyldimethylsilyloxy)-6-[(E)-2-tertbutyldiphenylsilyloxyethylidene]-3,3-dimethyl-10-(2-trimethylsilylethoxymethoxy)dodec-1-en-4-one

Guidance literature:: Multi-step reaction with 8 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

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