(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester
CAS No.:1246371-08-3
Molecular Formula:C₁₉H₃₄O₄Si
Molecular Weight:354.562
Hs Code.:

Synonyms:(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

There total 10 articles about (1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester 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: 60.0%

: 1246371-06-1
(1S,3R,5S)-5-but-3-enyl-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxo-cyclohexanecarboxylic acid methyl ester

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1246371-08-3
(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 0.166667h; Inert atmosphere;

(1S,3R,5S)-5-but-3-enyl-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxo-cyclohexanecarboxylic acid methyl ester; In trifluoroacetic acid; at -12 - 20 ℃; for 1.66667h;

Reference yield:

: 194999-04-7
(2S,3S,4aR,6R,8S,8aS)-6-hydroxy-8-iodo-2,3-dimethoxy-2,3-dimethyloctahydrobenzo[1,4]dioxine-6-carboxylic acid methyl ester

: 1246371-08-3
(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 70 - 110 °C

2.1: diisobutylaluminium hydride / toluene / 1.42 h / -70 - -30 °C

3.1: triphenylphosphine / Wilkinson's catalyst / isopropyl alcohol; hexane; tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / water / 1 h / 20 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 5 - 20 °C

6.1: Dess-Martin periodane / dichloromethane / 24 h / 20 °C

7.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere

7.2: 1.67 h / -12 - 20 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; Wilkinson's catalyst; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 7.1: Wittig Reaction;

Reference yield:

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 1246371-08-3
(1S,3R,5S)-5-(but-3'-enyl)-3-[(tert-butyldimethylsily)oxy]-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / toluene / 2.67 h / 20 - 110 °C

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 70 - 110 °C

3.1: diisobutylaluminium hydride / toluene / 1.42 h / -70 - -30 °C

4.1: triphenylphosphine / Wilkinson's catalyst / isopropyl alcohol; hexane; tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / water / 1 h / 20 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 5 - 20 °C

7.1: Dess-Martin periodane / dichloromethane / 24 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 0 °C / Inert atmosphere

8.2: 1.67 h / -12 - 20 °C

With 1H-imidazole; n-butyllithium; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; Wilkinson's catalyst; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 8.1: Wittig Reaction;