9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-

Base Information

• Chemical Name: 9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-
• CAS No.: 73-03-0
• Molecular Formula: C10H13N5O3
• Molecular Weight: 251.245
• Hs Code.: 29349990
• NSC Number: 627047,401022,89220,63984
• DSSTox Substance ID: DTXSID00859090
• Wikidata: Q104193318
• ChEMBL ID: CHEMBL42814
• Mol file: 73-03-0.mol

Synonyms:3-Deoxyadenosine;NSC63984;CHEMBL42814;MLS003389401;NSC401022;2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol;9-(.beta.-D-3'-Deoxyribofuranosyl)adenine;.beta.-D-erythro-Pentofuranoside, adenine-9 3-deoxy-;9H-Purine, 6-amino-9-(3-deoxy-.beta.-D-ribofuranosyl)-;BRD2581;9H-Purin-6-amine, 9-(3-deoxy-.beta.-D-erythro-pentofuranosyl)-;BRD-2581;MFCD00037998;NSC627047;9-(3-deoxypentofuranosyl)-9h-purin-6-amine;NSC-627047;2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol;3'-Deoxyadenosine (cordycepin);SCHEMBL20419171;DTXSID00859090;OFEZSBMBBKLLBJ-UHFFFAOYSA-N;HMS3268J08;HMS3372P05;BCP01713;NSC89220;BDBM50031231;NSC-89220;SB18953;NCI60_013263;SMR002049054;SY077107;3 inverted exclamation mark -Deoxyadenosine;BRD-A61362581-001-01-2;BRD-A61362581-001-02-0;2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol;9(3DeoxyDribofuranosyl)adenine;3Deoxyadenosine;5''-deoxyadenosine2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Chemical Property of 9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 225-229 °C
• Refractive Index: 1.7610 (estimate)
• Boiling Point: 627.2 °C at 760 mmHg
• PKA: 13?+-.0.60(Predicted)
• Flash Point: 333.1 °C
• PSA: 119.31000
• Density: 1.91 g/cm³
• LogP: -0.36960
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml).
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 251.10183929
• Heavy Atom Count: 18
• Complexity: 307

Purity/Quality:

95%-98% ^*data from raw suppliers

Cordycepin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 40-36/37/38-25-20/21/22
• Safety Statements: 22-36-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(C1O)N2C=NC3=C(N=CN=C32)N)CO
• Uses: Cordycepin is known to have various kinds of effects of improving immune skill, anti-aging, anti-fatigue, anti-cancer, anti-bacterial, anti-virus, lowering blood glucose and lipid and male hormone. First reported nucleoside antibiotic.
• Description: Cordycepin (73-03-0) is an adenosine analog lacking the hydroxyl at the 3’ position. Inhibits PARP1?and polyadenylation2. Displays anti-inflammatory effects1,3?and neuroprotective effects by inhibiting Aβ-induced apoptosis in hippocampal neurons4. Induces apoptosis in a variety of cancer cell lines5. Displays antiobesity effects.6?Inhibits cell senescence via activation of AMPK.7?Maintains stem cell pluripotency and increases iPS cell generation efficiency.8

Technology Process of 9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)-

There total 83 articles about 9H-Purine, 6-amino-9-(3-deoxy-beta-D-ribofuranosyl)- 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: 100.0%

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-6-chloropurine → cordycepin (73-03-0)

Guidance literature:

With ammonia; In methanol; ethanol; at -20 ℃; for 48h;

DOI:10.3390/molecules23061457

Reference yield: 98.0%

9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) → cordycepin (73-03-0)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; dimethyl sulfoxide; 1.) 4 deg C, 1 h, 2.) 19-22 deg C, overnight;

DOI:10.1021/jo00129a034

Reference yield: 95.0%

C14H16ClN5O5 → cordycepin (73-03-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 25 ℃; for 8h; under 37503.8 Torr;

upstream raw materials:

9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-erythro-pentofuranosyl>adenine

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate

6-N-5'-O-Bis-<4-methoxytriphenylmethyl>-3'-deoxyadenosine

Downstream raw materials:

9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine

N₆,2',5'-tribenzoyl-3'-deoxyadenosine

(2R,3R,5S)-2-[6-(N-benzoylbenzamido)-9H-purin-9-yl]-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate

3'-deoxy-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Refernces

Reactions of 2-acyloxyisobutyryl halides with nucleosides. I. Reactions of model diols and of uridine.

10.1021/ja00793a031

The research investigates the reactions of 2-acyloxyisobutyryl halides with various nucleosides, particularly focusing on adenosine and uridine. Key chemicals involved include 2-acetoxyisobutyryl chloride and the corresponding acyl bromide. For adenosine, the reaction with 2-acetoxyisobutyryl chloride in acetonitrile at 80°C yielded 9-(2-O-acetyl-3-chloro-3-deoxy-β-D-xylofuranosyl)adenine (4a) as a major product, with the 5'-hydroxy group present as a 2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl ether. This compound can be further processed to remove the dioxolanone and acetyl groups, leading to the formation of 2',3'-anhydroadenosine. The study also explores the formation of 9-(3-O-acetyl-2-chloro-2-deoxy-β-D-arabinofuranosyl)adenine (5) and the subsequent hydrogenolysis of related brominated compounds to produce 3'-deoxyadenosine (Cordycepin) and 2',3'-dideoxyadenosine. For uridine, the reaction with 2-acetoxyisobutyryl chloride leads to the formation of 3'-O-acetyl-2'-chloro-2'-deoxyuridine derivatives, with the overall cis stereochemistry influenced by the participation of the uracil ring's C2 carbonyl group.

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