[[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester

Base Information

• Chemical Name: [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester
• CAS No.: 862490-61-7
• Molecular Formula: C₂₃H₂₇N₇O₉S
• Molecular Weight: 577.575
• Mol file: 862490-61-7.mol

Synonyms:[[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester

Chemical Property of [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester

There total 2 articles about [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl 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: 73.0%

2-nitrobenzenesulfonyl glycine ethyl ester (313497-39-1) + 2',3'-isopropylidene adenosine (362-75-4) → [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester (862490-61-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1021/jo050205w

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester (862490-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / sodium carbonate / dioxane; H₂O / 16 h / 20 °C

2: 73 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

With sodium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; water; 2: Mitsunobu reaction;

DOI:10.1021/jo050205w

Reference yield:

[[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester (862490-61-7) → [[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester (862490-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA; H₂O / 3.5 h

2: 77 percent / triethylamine / tetrahydrofuran / 8 h

With water; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jo050205w

upstream raw materials:

2-nitrobenzenesulfonyl glycine ethyl ester

2',3'-isopropylidene adenosine

2-Nitrobenzenesulfonyl chloride

Downstream raw materials:

[[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester

[[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester