(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester

Base Information

Chemical Name:(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester
CAS No.:367270-55-1
Molecular Formula:C₄₂H₆₈O₇Si₂
Molecular Weight:741.169
Hs Code.:

(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester

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

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

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

There total 10 articles about (E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-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:

: 165258-10-6
(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-enal

: 367270-45-9
2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid tert-butyl ester

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

: 367270-55-1
(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/S0040-4039(01)01169-8

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 367270-55-1
(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / AgNO₃; pyridine / tetrahydrofuran / 0 °C

2: 50 percent / AgOTf; 2,6-di-tert-butyl-pyridine / CH₂Cl₂ / 0 - 20 °C

3: 85 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

4: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5: 77 percent / diethyl ether / -78 - 20 °C

6: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

With pyridine; 2,6-di-tert-butyl-pyridine; di-n-butylboryl trifluoromethanesulfonate; silver trifluoromethanesulfonate; Dess-Martin periodane; silver nitrate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; 4: Dess-Martin oxidation / 5: Grignard reaction / 6: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01169-8

Reference yield:

: 367270-46-0
(E)-(S)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid tert-butyl ester

: 367270-55-1
(E)-(2R,3S,4S,6R,7R,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-undec-8-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: AD-mix-α; H2O; MeSO2NH2 / 2-methyl-propan-2-ol / 0 - 20 °C

2: 85 percent / AgNO₃; pyridine / tetrahydrofuran / 0 °C

3: 50 percent / AgOTf; 2,6-di-tert-butyl-pyridine / CH₂Cl₂ / 0 - 20 °C

4: 85 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

5: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

6: 77 percent / diethyl ether / -78 - 20 °C

7: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

8: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

With pyridine; AD-mix-α; 2,6-di-tert-butyl-pyridine; methanesulfonamide; di-n-butylboryl trifluoromethanesulfonate; water; silver trifluoromethanesulfonate; Dess-Martin periodane; silver nitrate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 5: Dess-Martin oxidation / 6: Grignard reaction / 7: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(01)01169-8