(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

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Chemical Name:(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran
CAS No.:1369405-94-6
Molecular Formula:C₄₁H₃₉ClF₂O₅
Molecular Weight:685.207
Hs Code.:

Synonyms:(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

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Chemical Property of (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

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Technology Process of (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

There total 11 articles about (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran 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: 61.0%

: 333361-51-6
4-bromo-1-chloro-2-(4-methoxybenzyl)benzene

: 1369405-89-9
(3R,4R,6S)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one

: 1369405-94-6
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 1h; Inert atmosphere;

(3R,4R,6S)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -98 ℃; for 3h; stereoselective reaction; Further stages;
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

: 1369405-94-6
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 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

With potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;
DOI:10.1016/j.tetlet.2012.02.062

Reference yield:

: (2S,3R,5S)-2,3,6-tris(benzyloxy)-4,4-difluorohexane-1,5-diol

: 1369405-94-6
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

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

2.2: 3 h / -98 °C

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tetlet.2012.02.062