(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

Base Information

Chemical Name:(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester
CAS No.:903558-93-0
Molecular Formula:C₄₁H₇₄O₈Si₂
Molecular Weight:751.205
Hs Code.:

(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

Synonyms:(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

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Chemical Property of (E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

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Technology Process of (E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

There total 9 articles about (E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester 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: 78.0%

: 903558-92-9
(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 903558-93-0
(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃;
DOI:10.1016/j.tetlet.2006.04.044

Reference yield:

: (R)-3-(4-Methoxy-benzyloxy)-2-methyl-butyraldehyde

: 903558-93-0
(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 60 °C

2.1: 89 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3.1: 96 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 0 °C

4.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.2: 88 percent / CH₂Cl₂ / -78 - 0 °C

5.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Wittig olefination / 3.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.04.044

Reference yield:

: 903558-90-7
(S)-3-(4-Methoxy-benzyloxy)-2-methyl-butan-1-ol

: 903558-93-0
(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-11-(4-methoxy-benzyloxy)-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; Dess-Martin reagent / CH₂Cl₂

2.1: tetrahydrofuran / 60 °C

3.1: 89 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4.1: 96 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 0 °C

5.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.2: 88 percent / CH₂Cl₂ / -78 - 0 °C

6.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Dess-Martin oxidation / 2.1: Wittig olefination / 4.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.04.044