(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

Base Information

Chemical Name:(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene
CAS No.:1426146-04-4
Molecular Formula:C₅₀H₈₆O₈Si₃
Molecular Weight:899.485
Hs Code.:

(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

Synonyms:(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

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Chemical Property of (5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

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Technology Process of (5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

There total 16 articles about (5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene 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: 93.0%

: C₅₃H₉₆O₉Si₄

: 1426146-04-4
(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 ℃; for 0.0833333h;
DOI:10.1021/ol303515h

Reference yield:

: 1426145-91-6
(3R,5R)-5-((5S,6R)-6-(methoxymethoxy)-10,10-dimethyl-9,9-diphenyl-2,4,8-trioxa-9-silaundecan-5-yl)-3-methyldihydrofuran-2(3H)-one

: 1426146-04-4
(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

Guidance literature:: Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / dichloromethane; hexane; methanol / 1.33 h / -78 °C

2.1: acetonitrile / 20 h / Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 - 25 °C

4.1: 1H-imidazole / dichloromethane / 1 h / 0 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

6.1: 1H-imidazole / dichloromethane / 0.5 h / 0 °C

7.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 1 h / 0 °C

8.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 0 °C

9.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

9.2: 2 h / -78 °C / Inert atmosphere

10.1: pyridine; Dess-Martin periodane / dichloromethane / 2.5 h / 0 - 25 °C

11.1: diethyl ether; tetrahydrofuran / 1 h / -20 - 0 °C

12.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.08 h / 0 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 2.1: |Wittig Rearrangement / 11.1: |Peterson Olefination;
DOI:10.1021/ol303515h

Reference yield:

: 1426145-90-5
(3R,5R)-5-((1R,2R)-3-((tert-butyldiphenylsilyl)oxy)-1,2-dihydroxypropyl)-3-methyldihydrofuran-2(3H)-one

: 1426146-04-4
(5S,6R,10R,11R,E)-11-(tert-butyldimethylsilyloxy)-5-((2R,4R,5S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methyltetrahydrofuran-2-yl)-6-(methoxymethoxy)-9,10,14,14,15,15-hexamethyl-7-methylene-2,4,13-trioxa-14-silahexadec-8-ene

Guidance literature:: Multi-step reaction with 13 steps

1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 h / 0 - 60 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane; methanol / 1.33 h / -78 °C

3.1: acetonitrile / 20 h / Reflux

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 - 25 °C

5.1: 1H-imidazole / dichloromethane / 1 h / 0 °C

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

7.1: 1H-imidazole / dichloromethane / 0.5 h / 0 °C

8.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 1 h / 0 °C

9.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 0 °C

10.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

10.2: 2 h / -78 °C / Inert atmosphere

11.1: pyridine; Dess-Martin periodane / dichloromethane / 2.5 h / 0 - 25 °C

12.1: diethyl ether; tetrahydrofuran / 1 h / -20 - 0 °C

13.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.08 h / 0 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Wittig Rearrangement / 12.1: |Peterson Olefination;
DOI:10.1021/ol303515h