3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine

Base Information

• Chemical Name: 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine
• CAS No.: 262289-33-8
• Molecular Formula: C₃₇H₄₂F₂N₂O₈Si
• Molecular Weight: 708.831

Synonyms:3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine

Chemical Property of 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine

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Technology Process of 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine

There total 2 articles about 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine 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:

5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine (159755-13-2) → 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine (262289-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2: 0.39 g / zinc / tetrahydrofuran / 0.42 h / Heating

With Dess-Martin periodane; zinc; In tetrahydrofuran; dichloromethane; 1: Oxidation / 2: Substitution;

DOI:10.1016/S0040-4020(99)01007-8

Reference yield:

bromodifluoromethyl[tris(dimethylamino)]phosphonium bromide (58310-30-8) + 5'-O-dimethoxytrityl-3'-oxo-2'-O-trimethylsilylethoxymethyluridine (262289-32-7) → 3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine (262289-33-8)

Guidance literature:

With zinc; In tetrahydrofuran; for 0.416667h; Heating;

DOI:10.1016/S0040-4020(99)01007-8

Reference yield: 70.0%

3'-deoxy-3'-difluoromethylene-5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine (262289-33-8) → 1-(2,3-didehydro-2,3-dideoxy-5-O-dimethoxytrityl-3-C-trifluoromethyl-β-D-glycero-pentofuranosyl)uracil (262289-34-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 3h;

DOI:10.1016/S0040-4020(99)01007-8

upstream raw materials:

bromodifluoromethyl[tris(dimethylamino)]phosphonium bromide

5'-O-dimethoxytrityl-3'-oxo-2'-O-trimethylsilylethoxymethyluridine

5'-O-dimethoxytrityl-2'-O-trimethylsilylethoxymethyluridine

Downstream raw materials:

1-(2,3-didehydro-2,3-dideoxy-5-O-dimethoxytrityl-3-C-trifluoromethyl-β-D-glycero-pentofuranosyl)uracil

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