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

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Chemical Name:(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-3,3-difluorotetrahydro-2H-pyran
CAS No.:1369406-00-7
Molecular Formula:C₄₂H₄₂F₂O₅
Molecular Weight:664.789
Hs Code.:

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

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

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

There total 12 articles about (2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-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: 54.0%

: 333361-15-2
4-bromo-2-(4-methoxybenzyl)-1-methylbenzene

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

: 1369406-00-7
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: 4-bromo-2-(4-methoxybenzyl)-1-methylbenzene; 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:

: (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluorobut-3-en-1-ol

: 1369406-00-7
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 13 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

1.2: 0 - 20 °C

2.1: acetic acid / water / 3 h / 50 °C

3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C

4.2: 0 - 20 °C

5.1: 12 h / 130 °C

6.1: methanol; potassium carbonate / 8 h / 20 °C

7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

8.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

8.2: 0 - 20 °C

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

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

10.2: 16 h / Reflux

11.1: tetrabutyl ammonium fluoride / 0 - 20 °C

12.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

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

13.2: 3 h / -98 °C

With methanol; dmap; potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; mineral oil;
DOI:10.1016/j.tetlet.2012.02.062

Reference yield:

: 1005768-69-3
(2R,3R)-3-O-benzyl-4,4-difluoro-5-hexene-1,2,3-triol

: 1369406-00-7
(2S,4R,5S,6R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(3-(4-methoxybenzyl)-4-methylphenyl)-3,3-difluorotetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 11 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C

2.2: 0 - 20 °C

3.1: 12 h / 130 °C

4.1: methanol; potassium carbonate / 8 h / 20 °C

5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

6.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

6.2: 0 - 20 °C

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

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

8.2: 16 h / Reflux

9.1: tetrabutyl ammonium fluoride / 0 - 20 °C

10.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 0 - 20 °C

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

11.2: 3 h / -98 °C

With methanol; dmap; potassium osmate(VI) dihydrate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; mineral oil;
DOI:10.1016/j.tetlet.2012.02.062