(2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol

Base Information

• Chemical Name: (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol
• CAS No.: 1185750-32-6
• Molecular Formula: C₅₈H₈₆O₆Si₂
• Molecular Weight: 935.488

Synonyms:(2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol

Chemical Property of (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol

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Technology Process of (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol

There total 11 articles about (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol 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: 57.0%

(2S,3R,4S,5E,7E,9R,10S,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyltrideca-5,7-diene-3,9-diol (1185750-55-3) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol (1185750-32-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 1.33333h; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane (1185750-54-2) → (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol (1185750-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane / 1.33 h / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

(2R,3S,4S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-N,2,4-trimethylpentanamide (1158955-70-4) → (2S,3R,4S,5E,7E,9R,10R,11S,12S)-1-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)-11-(4-methoxybenzyloxy)-2,4,6,10,12-pentamethyl-9-(triisopropylsilyloxy)trideca-5,7-diene-3,9-diol (1185750-32-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 4 h / -30 - 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere; Reflux

4.1: triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride / diethyl ether; hexane; toluene / 2 h / -78 - -30 °C / Inert atmosphere

4.2: 2 h / -30 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 1.33 h / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; triisopropoxytitanium(IV) chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1016/j.tet.2009.04.073

upstream raw materials:

(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

(2S,4S,5R,6S)-4-ethynyl-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

(2R,3S,4S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-N,2,4-trimethylpentanamide

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