9-beta-D-Arabinosyladenine

Base Information

• Chemical Name: 9-beta-D-Arabinosyladenine
• CAS No.: 10563-76-5
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.244
• NSC Number: 118426,118425,114884,101171,90560
• DSSTox Substance ID: DTXSID90909639
• ChEMBL ID: CHEMBL39762
• Mol file: 10563-76-5.mol

Synonyms:9-beta-D-Arabinosyladenine;10563-76-5;9-pentopyranosyl-9h-purin-6-amine;NSC90560;Adenine, 9-.beta.-D-ribopyranosyl-;Adenine, 9-.alpha.-D-xylopyranosyl-;Adenine, 9-.beta.-D-arabinopyranosyl-;Adenine, 9-.alpha.-D-arabinopyranosyl-;Ribopyranoside, adenine-9;9H-Purin-6-amine, 9-.beta.-D-ribopyranosyl-;9H-Purin-6-amine, 9-.alpha.-D-xylopyranosyl-;NCIOpen2_005702;NCIOpen2_006932;9H-Purin-6-amine, 9-.beta.-D-arabinopyranosyl-;9H-Purin-6-amine, 9-.alpha.-D-arabinopyranosyl-;CHEMBL39762;SCHEMBL6672533;9-.beta.-D-Xylopyranosyladenin;9-.beta.-D-Ribopyranosyladenine;9-.beta.-D-Xylopyranosyladenine;DTXSID90909639;9-.alpha.-D-Xylopyranosyladenine;9-.beta.-D-Arabinopyranosyladenine;9-.alpha.-D-Arabinopyranosyladenine;Adenine, 9-.beta.-D-xylopyranosyl-;NSC-90560;NSC101171;NSC114884;NSC118425;NSC118426;NSC-101171;NSC-114884;NSC-118425;NSC-118426;9H-Purin-6-amine, 9-.beta.-D-xylopyranosyl-;17434-52-5;18031-19-1;18031-20-4;18031-28-2

Chemical Property of 9-beta-D-Arabinosyladenine

Chemical Property:

• Vapor Pressure: 3.14E-17mmHg at 25°C
• Boiling Point: 639.5°Cat760mmHg
• Flash Point: 340.6°C
• Density: 2.08g/cm³
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O)O

Technology Process of 9-beta-D-Arabinosyladenine

There total 6 articles about 9-beta-D-Arabinosyladenine 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: 70.0%

D-ribose (50-69-1) + 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) → 9-β-D-ribopyranosyladenine (10563-76-5)

Guidance literature:

adenine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

D-ribose; With tributylphosphine; di-isopropyl azodicarboxylate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12 - 16h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02332

Reference yield:

2,3,4-tri-O-acetyl-β-D-ribopyranosyl chloride (4049-36-9) → 9-β-D-ribopyranosyladenine (10563-76-5)

Guidance literature:

With xylene; Behandeln des Reaktionsprodukts mit methanol.NH₃;

DOI:10.1021/ja01126a066

Reference yield:

→ 9-β-D-ribopyranosyladenine (10563-76-5)

Guidance literature:

With pyridine; Behandeln des Reaktionsprodukts mit methanol.Natriummethylat;

DOI:10.1039/jr9460000852

upstream raw materials:

2,3,4-tri-O-acetyl-β-D-ribopyranosyl chloride

D-ribose

adenine

Downstream raw materials:

9-β-D-ribopyranosyl-1,9-dihydro-purin-6-one

Refernces

• 1、 Downey, A. Michael,Richter, Celin,Pohl, Radek,Mahrwald, Rainer,Hocek, Michal. "Direct One-Pot Synthesis of Nucleosides from Unprotected or 5-O-Monoprotected d -Ribose". supporting information. p. 4604 - 4607. Retrieved 2015/09/28.