(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

Base Information

Chemical Name:(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate
CAS No.:1449471-89-9
Molecular Formula:C₄₆H₈₀INO₇Si
Molecular Weight:914.134
Hs Code.:

(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

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Chemical Property of (7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

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Technology Process of (7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

There total 13 articles about (7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate 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:

: 909270-38-8
(E)-ethyl nonadec-4-enoate

: 1449471-89-9
(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 19 h / 0 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux

3.1: toluene-4-sulfonic acid / toluene / 60 °C

4.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: -78 - 20 °C

6.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / tert-butyl methyl ether / 5 h / -78 °C

6.2: 21 h / -78 °C / Reflux

7.1: triethylamine; dmap / tetrahydrofuran

With 1H-imidazole; dmap; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; triethylamine; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl methyl ether; water; toluene; tert-butyl alcohol; 5.1: |Wittig Olefination / 5.2: |Wittig Olefination;
DOI:10.1002/anie.201208403

Reference yield:

: 112-71-0
1-Bromotetradecane

: 1449471-89-9
(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: magnesium; iodine / diethyl ether / 2 h / 20 °C

1.2: 2 h / 0 - 20 °C

2.1: propionic acid / benzene / 2 h / 150 °C

3.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 19 h / 0 °C

4.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux

5.1: toluene-4-sulfonic acid / toluene / 60 °C

6.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

7.2: -78 - 20 °C

8.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / tert-butyl methyl ether / 5 h / -78 °C

8.2: 21 h / -78 °C / Reflux

9.1: triethylamine; dmap / tetrahydrofuran

With 1H-imidazole; dmap; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; magnesium; propionic acid; triethylamine; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl methyl ether; water; toluene; tert-butyl alcohol; benzene; 2.1: |Johnson-Claisen Rearrangement / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;
DOI:10.1002/anie.201208403

Reference yield:

: 909270-40-2
(R)-5-((R)-1-hydroxypentadecyl)-dihydrofuran-2(3H)-one

: 1449471-89-9
(7R,13R,Z)-13-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-14-iodotetradec-3-en-7-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux

2.1: toluene-4-sulfonic acid / toluene / 60 °C

3.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

4.2: -78 - 20 °C

5.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / tert-butyl methyl ether / 5 h / -78 °C

5.2: 21 h / -78 °C / Reflux

6.1: triethylamine; dmap / tetrahydrofuran

With 1H-imidazole; dmap; lithium aluminium tetrahydride; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; triethylamine; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl methyl ether; toluene; 4.1: |Wittig Olefination / 4.2: |Wittig Olefination;
DOI:10.1002/anie.201208403