methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

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Chemical Name:methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate
CAS No.:444885-20-5
Molecular Formula:C₂₆H₃₈O₅Si
Molecular Weight:458.67
Hs Code.:

Synonyms:

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Chemical Property of methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

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Technology Process of methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

There total 11 articles about methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 444885-20-5
methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: K₂CO₃; tetrabutylammonium bromide; CuI / dimethylformamide / 0.17 h / 20 °C

2.2: 93 percent / dimethylformamide / 60 h / 20 °C

3.1: 92 percent / 4-methylmorpholine 4-oxide; OsO₄; H₂O / tetrahydrofuran; acetone / 20 °C

4.1: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate / 0.5 h / 20 °C / 760 Torr

5.1: NaIO₄; tetra-butylammonium periodate / tetrahydrofuran; H₂O / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -20 °C

6.2: 3.6 g / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: 43 percent / pyridinium 4-methylbenzenesulfonate / methanol / 1 h

8.1: NaIO₄; tetrabutylammonium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

9.1: NaH / benzene / 0.08 h

9.2: 238 mg / benzene / 0.5 h

With 1H-imidazole; quinoline; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; tetrabutylammomium bromide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(02)00046-7

Reference yield:

: 149859-05-2
1-[2',2'-dimethyl-(4'R)-1',3'-dioxolan-4'-yl]-(1S)-3-butyn-1-ol

: 444885-20-5
methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: K₂CO₃; tetrabutylammonium bromide; CuI / dimethylformamide / 0.17 h / 20 °C

2.2: 93 percent / dimethylformamide / 60 h / 20 °C

3.1: 92 percent / 4-methylmorpholine 4-oxide; OsO₄; H₂O / tetrahydrofuran; acetone / 20 °C

4.1: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate / 0.5 h / 20 °C / 760 Torr

5.1: NaIO₄; tetra-butylammonium periodate / tetrahydrofuran; H₂O / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -20 °C

6.2: 3.6 g / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: 43 percent / pyridinium 4-methylbenzenesulfonate / methanol / 1 h

8.1: NaIO₄; tetrabutylammonium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

9.1: NaH / benzene / 0.08 h

9.2: 238 mg / benzene / 0.5 h

With 1H-imidazole; quinoline; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; tetrabutylammomium bromide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(02)00046-7

Reference yield:

: 444885-23-8
1,2,3-trideoxy-4-O-(tert-butyldimethylsilyl)-5,6-O-isopropylidene-D-erythro-hex-1-ynitol

: 444885-20-5
methyl (2E,4S,6Z)-12-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-9-hydroxydodeca-2,6-dien-10-ynoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: K₂CO₃; tetrabutylammonium bromide; CuI / dimethylformamide / 0.17 h / 20 °C

1.2: 93 percent / dimethylformamide / 60 h / 20 °C

2.1: 92 percent / 4-methylmorpholine 4-oxide; OsO₄; H₂O / tetrahydrofuran; acetone / 20 °C

3.1: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate / 0.5 h / 20 °C / 760 Torr

4.1: NaIO₄; tetra-butylammonium periodate / tetrahydrofuran; H₂O / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -20 °C

5.2: 3.6 g / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: 43 percent / pyridinium 4-methylbenzenesulfonate / methanol / 1 h

7.1: NaIO₄; tetrabutylammonium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

8.1: NaH / benzene / 0.08 h

8.2: 238 mg / benzene / 0.5 h

With quinoline; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; tetrabutylammomium bromide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; tetrabutylammonium periodite; 4-methylmorpholine N-oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(02)00046-7