(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Base Information

Chemical Name:(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
CAS No.:1181680-61-4
Molecular Formula:C₂₁H₂₃ClF₂O₄
Molecular Weight:412.861
Hs Code.:

Synonyms:(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

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Chemical Property of (2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

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Technology Process of (2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

There total 16 articles about (2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 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: 98.0%

: 1181680-60-3
C₂₇H₂₉ClF₂O₇

: 1181680-61-4
(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Guidance literature:: C₂₇H₂₉ClF₂O₇; With sodium methylate; In methanol; dichloromethane; for 1h;

With hydrogenchloride; In methanol; dichloromethane;

Reference yield: 83.0%

: 1181680-59-0
(2R,4R,5S,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

: 1181680-61-4
(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Guidance literature:: With palladium 10% on activated carbon; hydrogen; 1,2-dichloro-benzene; In methanol; ethyl acetate; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2012.02.062

Reference yield:

: 1369405-75-3
(((2S,3R)-2,3-bis(benzyloxy)-4,4-difluorohex-5-en-1-yl)oxy)(tert-butyl)dimethylsilane

: 1181680-61-4
(2S,3R,4R,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 48 h / 20 °C

2.1: di(n-butyl)tin oxide / toluene / 6 h / Reflux

2.2: 16 h / Reflux

3.1: tetrabutyl ammonium fluoride / 0 - 20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C / Inert atmosphere

5.2: 3 h / -98 °C

5.3: -98 - 20 °C

6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 1 h / -10 °C

7.1: palladium 10% on activated carbon; hydrogen; 1,2-dichloro-benzene / methanol; ethyl acetate / 12 h / 20 °C

With triethylsilane; potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; palladium 10% on activated carbon; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; 1,2-dichloro-benzene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1016/j.tetlet.2012.02.062