[3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate

Base Information

• Chemical Name: [3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS No.: 15830-77-0
• Molecular Formula: C₁₆H₁₉N₅O₇
• Molecular Weight: 393.356
• NSC Number: 111703,103560,76766
• DSSTox Substance ID: DTXSID20935885
• Mol file: 15830-77-0.mol

Synonyms:ARA-ATA;arabinofuranosyladenine-2',3',5'-triacetate;vidarabine 2',3',5'-triacetate

Chemical Property of [3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 393.12844796
• Heavy Atom Count: 28
• Complexity: 620

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)OC(=O)C)OC(=O)C

Technology Process of [3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate

There total 7 articles about [3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate 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:

1,2,3,5-tetra-O-acetyl-β-D-xylofuranose (23094-61-3) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → O2,O3,O5-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose (15830-77-0,953089-09-3)

Guidance literature:

With tin(IV) chloride; In acetonitrile; at 20 ℃; for 48h;

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + tetra-O-acetyl-D-xylofuranose (42927-46-8) → O2,O3,O5-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose (15830-77-0,953089-09-3)

Guidance literature:

With tin(IV) chloride; In acetonitrile;

DOI:10.1021/jo971741u

Reference yield:

D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → O2,O3,O5-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose (15830-77-0,953089-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Dowex 8x50W / 4.5 h / 20 °C

2: pyridine / 4 h / 20 °C

3: H₂SO₄ / acetic acid / 3 h / 20 °C

4: SnCl₄ / acetonitrile / 18 h / 20 °C

With pyridine; Dowex 8x50W; sulfuric acid; tin(IV) chloride; In acetic acid; acetonitrile;

DOI:10.1039/b414739a

upstream raw materials:

adenine

tetra-O-acetyl-D-xylofuranose

D-xylofuranose

methyl xylofuranoside

Downstream raw materials:

1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose

(2R,3R,4R,5S)-2-(6-Amino-purin-9-yl)-5-(4-methoxy-phenylsulfanylmethyl)-tetrahydro-furan-3,4-diol

3'-deoxy-3'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine

(2R,3S,4S,5R)-2-(6-Amino-purin-9-yl)-4-chloro-5-(4-methoxy-phenylsulfanylmethyl)-tetrahydro-furan-3-ol