(2S,3R,4R,6R)-2-(4-chloro-3-(4-isopropoxybenzyl)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-isopropoxybenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• CAS No.: 1181681-87-7
• Molecular Formula: C₂₂H₂₅ClF₂O₅
• Molecular Weight: 442.887

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (2S,3R,4R,6R)-2-(4-chloro-3-(4-isopropoxybenzyl)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: 90.0%

(2R,4R,5S,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-(4-chloro-3-(4-isopropoxybenzyl)phenyl)-3,3-difluorotetrahydro-2H-pyran (1369405-81-1) → (2S,3R,4R,6R)-2-(4-chloro-3-(4-isopropoxybenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (1181681-87-7)

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:

(3R,4R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5,5-difluorotetrahydro-2H-pyran-2-one (1369405-80-0) → (2S,3R,4R,6R)-2-(4-chloro-3-(4-isopropoxybenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (1181681-87-7)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 3 h / -98 °C

1.3: -98 - 20 °C

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

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

With triethylsilane; n-butyllithium; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; 1,2-dichloro-benzene; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2012.02.062

Reference yield:

(2R,3R)-3-O-benzyl-4,4-difluoro-5-hexene-1,2,3-triol (1005768-69-3) → (2S,3R,4R,6R)-2-(4-chloro-3-(4-isopropoxybenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (1181681-87-7)

Guidance literature:

Multi-step reaction with 13 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

11.3: -98 - 20 °C

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

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

With methanol; triethylsilane; dmap; 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; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; 1,2-dichloro-benzene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; mineral oil;

DOI:10.1016/j.tetlet.2012.02.062

upstream raw materials:

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

(S)-2-((R)-1-(benzyloxy)-2,2-difluorobut-3-en-1-yl)oxirane

(2S,3R)-3-(benzyloxy)-4,4-difluorohex-5-ene-1,2-diyl diacetate

C₁₃H₁₆F₂O₃

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