(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

Base Information

Chemical Name:(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene
CAS No.:1373432-48-4
Molecular Formula:C₄₆H₈₂O₆Si₂
Molecular Weight:787.324
Hs Code.:

(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

Synonyms:(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

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Chemical Property of (5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

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Technology Process of (5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

There total 22 articles about (5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-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: 78.0%

: Tebbe's reagent

: 1373432-32-6
(2S,6S)-6-allyl-2-((5R,9S,10R,12S,13S,E)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-en-5-yl)-2-methoxydihydro-2H-pyran-4(3H)-one

: 1373432-48-4
(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: In tetrahydrofuran; toluene; at -20 - 20 ℃;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-39-3
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butan-1-ol

: 1373432-48-4
(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: Multi-step reaction with 17 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

4.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

4.2: 1 h

5.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C

6.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h

6.2: 8 h / -78 - 20 °C

7.1: triethylamine / dichloromethane / 0 - 20 °C

8.1: lithium triethylborohydride / tetrahydrofuran / 20 °C

8.2: 0 °C

9.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux

10.1: diethyl ether / -78 °C

11.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / -78 °C

12.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

13.1: 2,6-dimethylpyridine / dichloromethane / 0 °C

14.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C

14.2: 3 h / -78 °C

15.1: triphenylphosphine hydrobromide / tetrahydrofuran; methanol / 0 °C

16.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Molecular sieve

17.1: tetrahydrofuran; toluene / -20 - 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; Hoveyda-Grubbs catalyst second generation; tetrapropylammonium perruthennate; 4,4'-di-tert-butylbiphenyl; triphenylphosphine hydrobromide; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene; 12.1: Parikh-Doering oxidation / 14.1: Aldol condensation / 14.2: Aldol condensation / 16.1: Ley oxidation;
DOI:10.1021/ol300785c

Reference yield:

: 1373432-20-2
(2S,3S)-2-methyl-3-(triisopropylsilyloxy)butyl methanesulfonate

: 1373432-48-4
(5R,9S,10R,12S,13S,E)-5-((2S,6S)-6-allyl-2-methoxy-4-methylenetetrahydro-2H-pyran-2-yl)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: Multi-step reaction with 16 steps

1.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

3.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

3.2: 1 h

4.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C

5.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h

5.2: 8 h / -78 - 20 °C

6.1: triethylamine / dichloromethane / 0 - 20 °C

7.1: lithium triethylborohydride / tetrahydrofuran / 20 °C

7.2: 0 °C

8.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux

9.1: diethyl ether / -78 °C

10.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / -78 °C

11.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

12.1: 2,6-dimethylpyridine / dichloromethane / 0 °C

13.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C

13.2: 3 h / -78 °C

14.1: triphenylphosphine hydrobromide / tetrahydrofuran; methanol / 0 °C

15.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Molecular sieve

16.1: tetrahydrofuran; toluene / -20 - 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; Hoveyda-Grubbs catalyst second generation; tetrapropylammonium perruthennate; 4,4'-di-tert-butylbiphenyl; triphenylphosphine hydrobromide; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene; 11.1: Parikh-Doering oxidation / 13.1: Aldol condensation / 13.2: Aldol condensation / 15.1: Ley oxidation;
DOI:10.1021/ol300785c