(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

Base Information

Chemical Name:(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one
CAS No.:1426146-01-1
Molecular Formula:C₄₉H₈₄O₉Si₃
Molecular Weight:901.457
Hs Code.:

(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

Synonyms:(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

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Chemical Property of (5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

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Technology Process of (5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

There total 14 articles about (5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-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: 80.0%

: C₄₉H₈₆O₉Si₃

: 1426146-01-1
(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 25 ℃; for 2.5h;
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

: 1426146-01-1
(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 2.1: |Wittig Rearrangement;
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

: 1426146-01-1
(5S,6S,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-2,4,13-trioxa-14-silahexadec-8-en-7-one

Guidance literature:: Multi-step reaction with 11 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

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