Technology Process of (9E,13E)-(2R,4S,8S)-6-Benzenesulfonyl-17-(tert-butyl-dimethyl-silanyloxy)-4,8,10,14-tetramethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-octadeca-9,13-dien-5-one
There total 21 articles about (9E,13E)-(2R,4S,8S)-6-Benzenesulfonyl-17-(tert-butyl-dimethyl-silanyloxy)-4,8,10,14-tetramethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-octadeca-9,13-dien-5-one 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:
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127750-73-6
(2R,4S,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-one
- Guidance literature:
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Multi-step reaction with 10 steps
1: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -60 °C
2: 1) Mg / 1) I2 / 1) THF, room temp.; 2) THF, room temp., 16 h
3: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C
4: DIBAL / toluene / 1 h / -90 °C
5: 1) Mg / 1) I2 / 1) THF, room temp.; 2) THF, room temp. 16 h
6: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C
7: DIBAL / toluene / 1 h / -90 °C
8: 85 percent / diethyl ether / -78 - -40 °C
9: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature
10: 1) BuLi / THF
With
1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide;
iodine;
In
diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203
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127750-73-6
(2R,4S,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-one
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1) Mg / 1) I2 / 1) THF, room temp.; 2) THF, room temp., 16 h
2: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C
3: DIBAL / toluene / 1 h / -90 °C
4: 1) Mg / 1) I2 / 1) THF, room temp.; 2) THF, room temp. 16 h
5: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C
6: DIBAL / toluene / 1 h / -90 °C
7: 85 percent / diethyl ether / -78 - -40 °C
8: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature
9: 1) BuLi / THF
With
1H-imidazole; n-butyllithium; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium;
iodine;
In
diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203
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-
127750-73-6
(2R,4S,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-one
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C
2: DIBAL / toluene / 1 h / -90 °C
3: 1) Mg / 1) I2 / 1) THF, room temp.; 2) THF, room temp. 16 h
4: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C
5: DIBAL / toluene / 1 h / -90 °C
6: 85 percent / diethyl ether / -78 - -40 °C
7: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature
8: 1) BuLi / THF
With
1H-imidazole; n-butyllithium; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium;
iodine;
In
diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203
