(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

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Chemical Name:(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene
CAS No.:919298-83-2
Molecular Formula:C₄₇H₉₀O₅Si₃
Molecular Weight:819.485
Hs Code.:

(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

Synonyms:(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

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Chemical Property of (+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

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Technology Process of (+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

There total 26 articles about (+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene 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: 91.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: (Z)-14,16-bis-(tert-butyldimethylsilanyloxy)-6-(4-methoxybenzyloxy)-5,7,11,13,15-pentamethylhexadeca-1,3-dien-8-ol

: 919298-83-2
(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/chem.201406252

Reference yield:

: 6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-en-4-ol

: 919298-83-2
(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

Guidance literature:: Multi-step reaction with 14 steps

1.1: OsO₄; NMO / 2-methyl-propan-2-ol; H₂O

2.1: NaIO₄ / acetone; H₂O

3.1: NaBH₄

4.1: 95 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

5.1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

6.1: 98 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 0 - 20 °C

7.1: 64 percent / p-TSA / methanol / 7 h / 0 - 20 °C

8.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

9.1: 80 percent / NaHMDS / dimethylformamide; toluene / -60 - 20 °C

10.1: 98 percent / H₂ / Pd/C / cyclohexane / 24 h / 25857.4 Torr

11.1: 99 percent / MgSO₄; PPTS / toluene / 72 h / 80 °C

12.1: DIBAL-H / CH₂Cl₂ / -78 - -45 °C

13.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 0 °C

14.1: CrCl₃ / tetrahydrofuran / 0 - 20 °C

14.2: 95 percent / KH / tetrahydrofuran / 2.5 h / 0 °C

With chromium chloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 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; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 8.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1021/ol062737k

Reference yield:

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

: 919298-83-2
(+)-1-methoxy-4-[(1S,2R,3R,6S,8S,9R,10S)-3,9,11-tris-(tert-butyldimethylsilanyloxy)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methylpenta-2,4-dienyl)undecyloxymethyl]benzene

Guidance literature:: Multi-step reaction with 10 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

With chromium chloride; 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; 3.1: Mitsunobu reaction / 9.1: Dess-Martin oxidation;
DOI:10.1021/ol062737k