Technology Process of (1S)-6-O-benzyl-2,4-dideoxy-1-C-{(2R,3R,7S,8S)-7-hydroxy-5-methylidene-3-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-8-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]nonan-2-yl}-5-O-(4-methoxybenzyl)-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol
There total 8 articles about (1S)-6-O-benzyl-2,4-dideoxy-1-C-{(2R,3R,7S,8S)-7-hydroxy-5-methylidene-3-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-8-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]nonan-2-yl}-5-O-(4-methoxybenzyl)-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol 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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![(2S,3S,7R,8S,9R,10R,11S,13R)-14-(benzyloxy)-13-[(4-methoxybenzyl)oxy]-8,10-dimethyl-5-methylidene-7-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-2-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]tetradecane-3,9,11-triol](/Databaselist/images/loading.webp)
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1298085-84-3
(2S,3S,7R,8S,9R,10R,11S,13R)-14-(benzyloxy)-13-[(4-methoxybenzyl)oxy]-8,10-dimethyl-5-methylidene-7-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-2-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]tetradecane-3,9,11-triol
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1298085-85-4
(1S)-6-O-benzyl-2,4-dideoxy-1-C-{(2R,3R,7S,8S)-7-hydroxy-5-methylidene-3-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-8-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]nonan-2-yl}-5-O-(4-methoxybenzyl)-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol
- Guidance literature:
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With
camphor-10-sulfonic acid;
for 0.333333h;
Inert atmosphere;
DOI:10.1002/chem.201003264
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1298085-85-4
(1S)-6-O-benzyl-2,4-dideoxy-1-C-{(2R,3R,7S,8S)-7-hydroxy-5-methylidene-3-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-8-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]nonan-2-yl}-5-O-(4-methoxybenzyl)-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: trimethylsilyl trifluoromethanesulfonate / toluene / 6 h / -78 °C / Inert atmosphere
1.2: 16 h / -78 °C / Inert atmosphere
1.3: 0.33 h / Inert atmosphere; Reflux
2.1: pentamethylbenzene,; boron trichloride / dichloromethane / -78 °C / Inert atmosphere
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 °C / Inert atmosphere
4.1: boron trifluoride diethyl etherate / dichloromethane / 2.5 h / -78 °C / Inert atmosphere
5.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere
7.1: methyllithium lithium bromide / 1,2-dimethoxyethane; diethyl ether / 0.75 h / -78 °C / Inert atmosphere
7.2: 1.5 h / -78 °C / Inert atmosphere
8.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / -40 - 20 °C / Inert atmosphere
9.1: camphor-10-sulfonic acid / 0.33 h / Inert atmosphere
With
methyllithium lithium bromide; trimethylsilyl trifluoromethanesulfonate; pentamethylbenzene,; camphor-10-sulfonic acid; diethyl methoxy borane; boron trifluoride diethyl etherate; boron trichloride; toluene-4-sulfonic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; toluene; acetonitrile;
4.1: Mukaiyama reaction;
DOI:10.1002/chem.201003264
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1298085-85-4
(1S)-6-O-benzyl-2,4-dideoxy-1-C-{(2R,3R,7S,8S)-7-hydroxy-5-methylidene-3-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-8-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]nonan-2-yl}-5-O-(4-methoxybenzyl)-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol
- Guidance literature:
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Multi-step reaction with 8 steps
1.1: pentamethylbenzene,; boron trichloride / dichloromethane / -78 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: boron trifluoride diethyl etherate / dichloromethane / 2.5 h / -78 °C / Inert atmosphere
4.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: toluene-4-sulfonic acid / 0.5 h / 20 °C / Inert atmosphere
6.1: methyllithium lithium bromide / 1,2-dimethoxyethane; diethyl ether / 0.75 h / -78 °C / Inert atmosphere
6.2: 1.5 h / -78 °C / Inert atmosphere
7.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / -40 - 20 °C / Inert atmosphere
8.1: camphor-10-sulfonic acid / 0.33 h / Inert atmosphere
With
methyllithium lithium bromide; pentamethylbenzene,; camphor-10-sulfonic acid; diethyl methoxy borane; boron trifluoride diethyl etherate; boron trichloride; toluene-4-sulfonic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; acetonitrile;
3.1: Mukaiyama reaction;
DOI:10.1002/chem.201003264
