3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester
• CAS No.: 134760-62-6
• Molecular Formula: C₂₂H₂₂F₃N₅O₁₀S
• Molecular Weight: 605.505
• Mol file: 134760-62-6.mol

Synonyms:3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Chemical Property of 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

There total 5 articles about 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 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: 75.0%

3-(Trifluoromethyl)benzoyl chloride (2251-65-2) + 2-Amino-9-(3-O-mesyl-5-O-(methoxycarbonyl)-β-D-xylofuranosyl)-6-methoxy-9H-purine (134760-76-2) → 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-62-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; 1) ice bath cooling, 30 min, 2) rt, 2 h;

DOI:10.1016/S0040-4039(00)93545-7

Reference yield:

3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside (5432-33-7) → 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-62-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / NEt₃ / CH₂Cl₂ / 1) rt, 1.5 h, 2) 4 deg C, 16 h

2: 76 percent / conc. H₂SO₄, glacial acetic acid / 16 h / Ambient temperature

3: 1) N,O-bis(trimethylsilyl)acetamide, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, 80 deg C, 2) toluene, 80 deg C, 2 h, then rt, overnight

4: 80 percent / acetyl chloride / 18 h / Ambient temperature

5: 75 percent / NEt₃, DMAP / CH₂Cl₂ / 1) ice bath cooling, 30 min, 2) rt, 2 h

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; triethylamine; acetyl chloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)93545-7

Reference yield:

1,2-O-isopropylidene-3-O-mesyl-5-O-(methoxycarbonyl)-α-D-xylofuranose (74595-09-8) → 3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-62-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / conc. H₂SO₄, glacial acetic acid / 16 h / Ambient temperature

2: 1) N,O-bis(trimethylsilyl)acetamide, 2) trimethylsilyl triflate / 1) 1,2-dichloroethane, 80 deg C, 2) toluene, 80 deg C, 2 h, then rt, overnight

3: 80 percent / acetyl chloride / 18 h / Ambient temperature

4: 75 percent / NEt₃, DMAP / CH₂Cl₂ / 1) ice bath cooling, 30 min, 2) rt, 2 h

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; triethylamine; acetyl chloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)93545-7

upstream raw materials:

3-(Trifluoromethyl)benzoyl chloride

2-Amino-9-(3-O-mesyl-5-O-(methoxycarbonyl)-β-D-xylofuranosyl)-6-methoxy-9H-purine

3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside

1,2-O-isopropylidene-3-O-mesyl-5-O-(methoxycarbonyl)-α-D-xylofuranose