(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

Base Information

Chemical Name:(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol
CAS No.:1298085-88-7
Molecular Formula:C₄₆H₆₉F₃O₈
Molecular Weight:807.044
Hs Code.:

(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

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Chemical Property 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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

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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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

There total 7 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}-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:

Reference yield: 32.0%

: 1298085-87-6
(2R,4S,5R,6R,7S,8R,12S,13S)-1-(benzyloxy)-5,77-dimethyl-10-methylidene-8-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-13-[(4S,5S,6R)-2,2,5-trimethyl-6-(propan-2-yl)-1,3-dioxan-4-yl]tetradecane-2,4,6,12-tetrol

: 1298085-88-7
(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

Guidance literature:: With pyridinium p-toluenesulfonate; copper(II) sulfate; In acetone; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/chem.201003264

Reference yield:

: C₂₂H₂₁F₃O₃

: 1298085-88-7
(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

Guidance literature:: Multi-step reaction with 10 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: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

10.1: pyridinium p-toluenesulfonate; copper(II) sulfate / acetone / 0 - 20 °C / Inert atmosphere

With methyllithium lithium bromide; trimethylsilyl trifluoromethanesulfonate; pentamethylbenzene,; diethyl methoxy borane; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; boron trichloride; toluene-4-sulfonic acid; copper(II) sulfate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; acetone; toluene; acetonitrile; 4.1: Mukaiyama reaction;
DOI:10.1002/chem.201003264

Reference yield:

: 1298085-71-8
(2Z,4R,5R,9S,10S,11Z)-11-(benzoyloxy)-4,10-dimethyl-7-methylene-9-[(1S)-1-phenylethoxy]-5-{(1R)-1-[4-(trifluoromethyl)phenyl]ethoxy}-2,11-tridecadien-3-yl benzoate

: 1298085-88-7
(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}-2-methyl-1,3-O-(1-methylethylidene)-L-arabino-hexitol

Guidance literature:: Multi-step reaction with 9 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: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

9.1: pyridinium p-toluenesulfonate; copper(II) sulfate / acetone / 0 - 20 °C / Inert atmosphere

With methyllithium lithium bromide; pentamethylbenzene,; diethyl methoxy borane; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; boron trichloride; toluene-4-sulfonic acid; copper(II) sulfate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetic acid; acetone; acetonitrile; 3.1: Mukaiyama reaction;
DOI:10.1002/chem.201003264