2',3'-Di-O-acetyladenosine

Base Information

• Chemical Name: 2',3'-Di-O-acetyladenosine
• CAS No.: 29886-19-9
• Molecular Formula: C14H17N5O6
• Molecular Weight: 351.319
• European Community (EC) Number: 249-929-5
• DSSTox Substance ID: DTXSID00952338
• Nikkaji Number: J286.983G
• Wikidata: Q82930900
• Mol file: 29886-19-9.mol

Synonyms:2',3'-Di-O-acetyladenosine;29886-19-9;Adenosine 2',3'-diacetate;2',3'-Diacetyladenosine;EINECS 249-929-5;(2R,3R,4R,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl diacetate;[(2R,3R,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate;2'-O,3'-O-Diacetyladenosine;C14-H17-N5-O6;SCHEMBL6222404;DTXSID00952338;C14H17N5O6;2',3'-Di-O-acetyladenosine, >=99%;A820095;J-017681;9-(2,3-di-O-acetylpentofuranosyl)-9H-purin-6-amine;(2R,3R,4R,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyldiacetate;(2R,3R,4R,5R)-4-(acetyloxy)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl acetate

Chemical Property of 2',3'-Di-O-acetyladenosine

Chemical Property:

• Boiling Point: 599°Cat760mmHg
• Flash Point: 316.1°C
• PSA: 151.68000
• Density: 1.72g/cm³
• LogP: -0.25720
• Storage Temp.: −20°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 351.11788328
• Heavy Atom Count: 25
• Complexity: 522

Purity/Quality:

97% ^*data from raw suppliers

2',3'-Di-O-acetyladenoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(OC(C1OC(=O)C)N2C=NC3=C(N=CN=C32)N)CO
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H](O[C@H]([C@@H]1OC(=O)C)N2C=NC3=C(N=CN=C32)N)CO

Technology Process of 2',3'-Di-O-acetyladenosine

There total 11 articles about 2',3'-Di-O-acetyladenosine 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: 89.0%

triacetyladenosine (7387-57-7,953089-09-3) → 2',3'-di-O-acetyladenosine (29886-19-9)

Guidance literature:

With immobilized Pseudomonas fluorescens lipase; In acetonitrile; at 20 ℃; for 24h; pH=7.0; regioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/ejoc.200801096

Reference yield: 64.0%

(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-(((4-methoxyphenyl)diphenylmethoxy)methyl)tetrahydrofuran-3,4-diyl diacetate → 2',3'-di-O-acetyladenosine (29886-19-9)

Guidance literature:

With water; acetic acid; at 20 ℃; for 12h;

DOI:10.1021/acs.jmedchem.6b01190

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine (151928-74-4) → 2',3'-di-O-acetyladenosine (29886-19-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 3h;

DOI:10.1039/c0ob00104j

upstream raw materials:

5'-O-(triphenylmethyl)adenosine

acetic anhydride

triacetyladenosine

adenosine

Downstream raw materials:

5'-adenosine monophosphate

AMP-Amidate

adenyl(3'-5')phophoadenine

adenylyl(3'-5')phosphoadenine