6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Base Information

Chemical Name:6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one
CAS No.:370561-98-1
Molecular Formula:C₄₁H₇₀O₈Si₂
Molecular Weight:747.173
Hs Code.:

6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Synonyms:6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

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Chemical Property of 6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

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Technology Process of 6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

There total 14 articles about 6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one 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: 95.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 370561-96-9
(E)-(2S,3R,4S,5R,6R,10R)-6-[4-(tert-butyldimethylsilanyloxy)-2-hydroxy-6-methoxy-10-(4-methoxyphenoxy)-3,5,8-trimethyldodeca-7,11-dienyl]-2,2-dimethyl[1,3]dioxin-4-one

: 370561-98-1
6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Guidance literature:: With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja011424b DOI:10.1021/ja0205232

Reference yield:

: (2S,3S)-tert-butyldimethylsilyl-2-methylhex-4-yn-3-ol

: 370561-98-1
6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 92 percent / Ag₂O / diethyl ether / 3.5 h / 20 °C

2.1: 85 percent / CpRu(NCMe)3PF₆ / acetone / 0.33 h / 20 °C

3.1: (-)-(1S,2S)-(2'-Ph₂P-C₆H₄-CONH)2-1,2-diphenylethane; Pd₂dba3*CHCl₃; nBu₄NCl / CH₂Cl₂ / 20 h / 20 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

5.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 5 h / 0 °C

6.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

6.2: 82 percent / tetrahydrofuran / 3 h / -107 °C

7.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: 79 percent / DIBAL-H / toluene / 4 h / -78 °C

9.1: 94 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.75 h / -78 °C

10.1: 95 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 2,6-di-tert-butyl-pyridine; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; (-)-(1S,2S)-(2'-Ph₂P-C₆H₄-CONH)2-1,2-diphenylethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; 2.1: Alder-ene reaction;
DOI:10.1021/ja0205232

Reference yield:

: 370561-80-1
(S)-3-tert-butyldimethylsilyloxy-2-methylhex-4-yne-3-one

: 370561-98-1
6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / 2-methyl (S)-CBS oxazaborolidine; BH₃*SMe₂ / tetrahydrofuran / 1 h / -30 °C

2.1: 92 percent / Ag₂O / diethyl ether / 3.5 h / 20 °C

3.1: 85 percent / CpRu(NCMe)3PF₆ / acetone / 0.33 h / 20 °C

4.1: (-)-(1S,2S)-(2'-Ph₂P-C₆H₄-CONH)2-1,2-diphenylethane; Pd₂dba3*CHCl₃; nBu₄NCl / CH₂Cl₂ / 20 h / 20 °C

5.1: 96 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

6.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 5 h / 0 °C

7.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

7.2: 82 percent / tetrahydrofuran / 3 h / -107 °C

8.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9.1: 79 percent / DIBAL-H / toluene / 4 h / -78 °C

10.1: 94 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.75 h / -78 °C

11.1: 95 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 2,6-di-tert-butyl-pyridine; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; dimethylsulfide borane complex; (-)-(1S,2S)-(2'-Ph₂P-C₆H₄-CONH)2-1,2-diphenylethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; silver(l) oxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; 3.1: Alder-ene reaction;
DOI:10.1021/ja0205232