7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester

Base Information

• Chemical Name: 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester
• CAS No.: 919298-99-0
• Molecular Formula: C₆₆H₁₂₂O₈Si₄
• Molecular Weight: 1156.03

Synonyms:7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester

Chemical Property of 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester

There total 41 articles about 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl 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: 99.0%

(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,16S,19R,21S,22S,23Z)-9-hydroxy-21-(4-methoxy-benzyloxy)-7,13,19-tris(tert-butyldimethylsilyloxy)-6,12,14,16,20,22-hexamethyl-hexaeicosa-2,4,10,23,25-pentaenoic acid ethyl ester (919298-85-4) + t-butyldimethylsiyl triflate (69739-34-0) → 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester (919298-99-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ol062737k

Reference yield:

5,6-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-hexanal → 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester (919298-99-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: NaBH₄

2.1: 95 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

3.1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

4.1: 98 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: 64 percent / p-TSA / methanol / 7 h / 0 - 20 °C

6.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

7.1: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

8.1: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

9.1: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

10.1: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

11.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

12.1: CrCl₃ / tetrahydrofuran / 0 - 20 °C

12.2: 95 percent / KH / tetrahydrofuran / 2.5 h / 0 °C

13.1: 84 percent / p-TSA / methanol / 1.5 h / 0 °C

14.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

15.1: 75 percent / NaHMDS; HMPA / tetrahydrofuran; toluene / -78 - 20 °C

16.1: 66 mg / t-BuLi; Me₂Zn / pentane; diethyl ether; toluene / 1 h / -78 °C

17.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; chromium chloride; sodium tetrahydroborate; hydrogen; dimethyl zinc(II); tert.-butyl lithium; 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; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; pentane; 6.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation / 14.1: Dess-Martin oxidation / 15.1: Wittig reaction;

DOI:10.1021/ol062737k

Reference yield:

1,3-bis(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyl-pentane (919298-77-4) → 7,9,13,19-tetrakis-(tert-butyl-dimethyl-silanyloxy)-21-(4-methoxy-benzyloxy)-6,12,14,16,20,22-hexamethyl-hexacosa-2,4,10,23,25-pentaenoic acid ethyl ester (919298-99-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 93 percent / LiCl; n-BuLi; diisopropylamine / tetrahydrofuran / 32 h / 0 - 20 °C

2.1: 91 percent / n-BuLi; diisopropylamine; BH₃*NH₃ / tetrahydrofuran; hexane / 0 - 20 °C

3.1: 100 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

4.1: 93 percent / NaHCO₃; m-CPBA / CH₂Cl₂ / 16 h / 20 °C

5.1: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

6.1: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

7.1: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

8.1: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

9.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

10.1: CrCl₃ / tetrahydrofuran / 0 - 20 °C

10.2: 95 percent / KH / tetrahydrofuran / 2.5 h / 0 °C

11.1: 84 percent / p-TSA / methanol / 1.5 h / 0 °C

12.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

13.1: 75 percent / NaHMDS; HMPA / tetrahydrofuran; toluene / -78 - 20 °C

14.1: 66 mg / t-BuLi; Me₂Zn / pentane; diethyl ether; toluene / 1 h / -78 °C

15.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; chromium chloride; n-butyllithium; borane-ammonia complex; hydrogen; dimethyl zinc(II); tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; pentane; 3.1: Mitsunobu reaction / 9.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation / 13.1: Wittig reaction;

DOI:10.1021/ol062737k

upstream raw materials:

(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,16S,19R,21S,22S,23Z)-9-hydroxy-21-(4-methoxy-benzyloxy)-7,13,19-tris(tert-butyldimethylsilyloxy)-6,12,14,16,20,22-hexamethyl-hexaeicosa-2,4,10,23,25-pentaenoic acid ethyl ester

t-butyldimethylsiyl triflate

(3R,4S)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-1-hexyne

ethyl (2Z,4E,6R,7S)-7,9-bis{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-2,4-nonadienoate

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