5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

Base Information

Chemical Name:5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal
CAS No.:919298-95-6
Molecular Formula:C₄₄H₈₆O₆Si₃
Molecular Weight:795.42
Hs Code.:

5,11,13-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

Synonyms:5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

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Chemical Property of 5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

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Technology Process of 5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

There total 25 articles about 5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal 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: 97.0%

: 919298-94-5
5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecan-1-ol

: 919298-95-6
5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1021/ol062737k

Reference yield:

: 919298-77-4
1,3-bis(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyl-pentane

: 919298-95-6
5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / LiCl; n-BuLi; diisopropylamine / tetrahydrofuran / 32 h / 0 - 20 °C

2: 91 percent / n-BuLi; diisopropylamine; BH₃*NH₃ / tetrahydrofuran; hexane / 0 - 20 °C

3: 100 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

4: 93 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 16 h / 20 °C

5: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

6: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

7: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

8: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

9: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

With n-butyllithium; borane-ammonia complex; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 3: Mitsunobu reaction / 9: Dess-Martin oxidation;
DOI:10.1021/ol062737k

Reference yield:

: 5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexanal

: 919298-95-6
5,11,13-tris-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,8,10,12-pentamethyl-tridecanal

Guidance literature:: Multi-step reaction with 11 steps

1: NaBH₄

2: 95 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

3: 90 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

4: 98 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5: 64 percent / p-TSA / methanol / 7 h / 0 - 20 °C

6: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

7: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

8: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

9: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

10: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

11: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

With sodium tetrahydroborate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 6: Dess-Martin oxidation / 11: Dess-Martin oxidation;
DOI:10.1021/ol062737k