(3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone

Base Information

• Chemical Name: (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone
• CAS No.: 1027745-76-1
• Molecular Formula: C₃₅H₃₄F₂O₅
• Molecular Weight: 572.649
• Mol file: 1027745-76-1.mol

Synonyms:(3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone

Chemical Property of (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone

There total 22 articles about (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone 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:

(1S,3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanol → (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone (1027745-76-1) + C35H36F2O6 (1413374-91-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone (1027745-76-1) + C35H36F2O6 (1413374-91-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene; tetrahydrofuran / 3.67 h / 0 - 50 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 - -40 °C / Inert atmosphere

2.2: 2.25 h / -78 - 20 °C

3.1: L-proline / dimethyl sulfoxide / 8 h / 50 °C

4.1: pyridine; trichlorophosphate / 0 - 20 °C

5.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / -23 °C

5.2: 0.75 h

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 12 h / 40 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.2: 2 h / 0 - 20 °C

8.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

9.1: hydrogenchloride; methanol / dichloromethane / 20 °C

10.1: pyridine / dmap / dichloromethane / 0.75 h / 0 °C / Inert atmosphere

11.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / 20 °C / Inert atmosphere

12.1: sodium methylate; methanol / 20 °C / Industry scale

13.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; methanol; oxalyl dichloride; diethylamino-sulfur trifluoride; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; sodium methylate; Dess-Martin periodane; dimethyl sulfoxide; L-proline; trichlorophosphate; dmap; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-[(benzyl)methyl]-2,2-difluorocyclohexanone (1027745-76-1) + C35H36F2O6 (1413374-91-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 0 °C

1.3: cooling with ice

2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C

3.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

3.2: -78 - 0 °C

4.1: potassium carbonate / 18-crown-6 ether / toluene / 20 °C

5.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / -23 °C

5.2: 0.75 h

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 12 h / 40 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.2: 2 h / 0 - 20 °C

8.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

9.1: hydrogenchloride; methanol / dichloromethane / 20 °C

10.1: pyridine / dmap / dichloromethane / 0.75 h / 0 °C / Inert atmosphere

11.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / 20 °C / Inert atmosphere

12.1: sodium methylate; methanol / 20 °C / Industry scale

13.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; methanol; sodium tetrahydroborate; n-butyllithium; diethylamino-sulfur trifluoride; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; sodium methylate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; trifluoroacetic anhydride; dmap; 18-crown-6 ether; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one

(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

Downstream raw materials:

({[(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-[(benzyloxy)methyl]-4-(difluoromethylene)-3,3-difluorocyclohexyl]oxy}methyl)benzene