(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

Base Information

Chemical Name:(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate
CAS No.:1303438-66-5
Molecular Formula:C₃₈H₆₄O₉Si
Molecular Weight:693.006
Hs Code.:

Synonyms:(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

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Chemical Property of (5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

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Technology Process of (5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

There total 14 articles about (5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate 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: 94.0%

: 1003890-51-4
(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triol

: 108-24-7
acetic anhydride

: 1303438-66-5
(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo2003506

Reference yield:

: 887143-81-9
(1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide

: 1303438-66-5
(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

Guidance literature:: Multi-step reaction with 11 steps

1.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere

2.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere

3.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

6.1: pyridine; ozone / methanol; dichloromethane / -78 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: magnesium / diethyl ether / -78 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

9.1: cerium(III) chloride heptahydrate / water; acetonitrile / Inert atmosphere

10.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 °C / Inert atmosphere

11.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; cerium(III) chloride heptahydrate; diethyl methoxy borane; 2-nitrobenzenesulfonyl hydrazide; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; magnesium; triethylamine; In tetrahydrofuran; methanol; diethyl ether; 1,1-dichloroethane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo2003506

Reference yield:

: 887343-98-8
(4R,6R)-2-Allyloxy-4,6-divinyl-[1,3,2]dioxaphosphinane 2-oxide

: 1303438-66-5
(5S,7R,9S,12R,13S,14R)-15-(tert-butyldimethylsilyloxy)-13-(4-methoxybenzyloxy)-2,12,14-trimethylpentadec-1-ene-5,7,9-triyl triacetate

Guidance literature:: Multi-step reaction with 12 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane

2.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere

3.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere

4.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

6.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

7.1: pyridine; ozone / methanol; dichloromethane / -78 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: magnesium / diethyl ether / -78 °C / Inert atmosphere

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere

10.1: cerium(III) chloride heptahydrate / water; acetonitrile / Inert atmosphere

11.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 °C / Inert atmosphere

12.1: pyridine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; cerium(III) chloride heptahydrate; diethyl methoxy borane; 2-nitrobenzenesulfonyl hydrazide; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; magnesium; triethylamine; In tetrahydrofuran; methanol; diethyl ether; 1,1-dichloroethane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo2003506