Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester
• CAS No.: 134760-59-1
• Molecular Formula: C₃₀H₃₀N₆O₁₂S
• Molecular Weight: 698.667
• Mol file: 134760-59-1.mol

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-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 Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

There total 3 articles about Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-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:

3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside (5432-33-7) → Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-59-1)

Guidance literature:

Multi-step reaction with 3 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

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; triethylamine; 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) → Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-59-1)

Guidance literature:

Multi-step reaction with 2 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

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid;

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

Reference yield:

N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) + Acetic acid (2R,3R,4S,5R)-2-acetoxy-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (138383-69-4) → Acetic acid (2R,3R,4S,5R)-2-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester (134760-59-1)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; Yield given. Multistep reaction; 1) 1,2-dichloroethane, 80 deg C, 2) toluene, 80 deg C, 2 h, then rt, overnight;

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

upstream raw materials:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

Acetic acid (2R,3R,4S,5R)-2-acetoxy-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

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

Downstream raw materials:

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

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