Ara-ata

Base Information

• Chemical Name: Ara-ata
• CAS No.: 15830-52-1
• Molecular Formula: C16H19 N5 O7
• Molecular Weight: 393.356
• Nikkaji Number: J81.890I
• Mol file: 15830-52-1.mol

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

Chemical Property of Ara-ata

Chemical Property:

• Melting Point: 142 °C(Solv: ethanol (64-17-5))
• Boiling Point: 594.1°Cat760mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 313.1°C
• PSA: 157.75000
• Density: 1.62g/cm³
• LogP: 0.31360
• 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:

98%min ^*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
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)OC(=O)C)OC(=O)C

Technology Process of Ara-ata

There total 4 articles about Ara-ata 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: 95.0%

acetic anhydride (108-24-7) + arabinosyl adenine (5536-17-4) → (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (15830-52-1,953089-09-3)

Guidance literature:

arabinosyl adenine; With dmap; triethylamine; In acetonitrile; for 0.5h;

acetic anhydride; at 5 - 60 ℃; for 4h;

DOI:10.3987/COM-15-13350

Reference yield: 76.0%

6-N,N-diacetyl-9-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)adenine → (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (15830-52-1,953089-09-3)

Guidance literature:

In methanol; at 105 ℃; for 1.5h;

DOI:10.1021/jo051256w

Reference yield: 47.0%

N-Acetylimidazole (2466-76-4) + arabinosyl adenine (5536-17-4) → (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (15830-52-1,953089-09-3)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 4h; pH=8;

DOI:10.1055/s-0036-1588626

upstream raw materials:

acetic anhydride

arabinosyl adenine

N-Acetylimidazole

Downstream raw materials:

(2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

arabinosyl adenine

9-<2,3-di-O-acetyl-β-D-arabinofuranosyl>adenine

9-(2-O-acetyl-β-D-arabinofuranosyl)adenine

Refernces

• 1、 -. "A method for synthesizing nelarabine". Paragraph 0027; 0028. . Retrieved 2018/02/22.
• 2、 Xia, Ran,Sun, Li-Ping,Qu, Gui-Rong. "Synthesis of nelarabine with pure β-anomer through late-stage C-H nitration/nitro-reduction". . p. 2386 - 2393. Retrieved 2016/03/01.