9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine

Base Information

• Chemical Name: 9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine
• CAS No.: 10414-81-0
• Molecular Formula: C10H14N6O3
• Molecular Weight: 266.26
• Hs Code.: 2934999090
• NSC Number: 324326,121182,106048,106047
• DSSTox Substance ID: DTXSID70908822
• Wikidata: Q72435554
• ChEMBL ID: CHEMBL1373519
• Mol file: 10414-81-0.mol

Synonyms:9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine;NSC121182;MLS000737527;4-amino-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol;24807-84-9;9H-Purin-6-amine, 9-(2-amino-2-deoxy-.beta.-D-xylofuranosyl)-;24807-85-0;NSC-121182;JCI-2172;NSC106047;ADENOSINE,-2'-DEOXY;CHEMBL1373519;DTXSID70908822;HMS2270P24;NSC106048;NSC324326;NSC-106047;NSC-106048;NSC-324326;NCI60_000497;PD040975;SMR000528550;FT-0774323;9-(2-Amino-2-deoxypentofuranosyl)-9H-purin-6-amine;Adenine, 9-(2-amino-2-deoxy-.alpha.-D-xylofuranosyl)-

Chemical Property of 9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine

Chemical Property:

• Melting Point: 190-191 °C
• Boiling Point: 657.6 °C at 760 mmHg
• PKA: 13.42±0.70(Predicted)
• Flash Point: 351.5 °C
• PSA: 145.33000
• Density: 2.08 g/cm³
• LogP: -0.73210
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Soluble in DMSO.
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 266.11273833
• Heavy Atom Count: 19
• Complexity: 334

Purity/Quality:

98%,99%, ^*data from raw suppliers

2''-Amino-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)N)N
• Uses: 2'-AdA can be used as starting material for the synthesis of 2'-amino nucleotides.

Technology Process of 9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine

There total 20 articles about 9-(2-Amino-2-deoxy-d-xylofuranosyl) adenine 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: 75.0%

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) + 1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil (26889-39-4,56888-92-7,68115-81-1) → 2'-amino-2'-deoxyadenosine (10414-81-0)

Guidance literature:

In water; at 63 ℃; for 15h; in the presence of Enterobacter aerogenes, and KH₂PO₄;

Reference yield:

2'-Azido-2'-deoxyadenosine (58699-61-9,29411-71-0) → 2'-amino-2'-deoxyadenosine (10414-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / pyridine / Ambient temperature

2: 94 percent / Bu₃SnH, AIBN / toluene / 2.5 h / 115 °C

3: TBAF / tetrahydrofuran

With pyridine; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; toluene;

DOI:10.1021/ja962117m

Reference yield:

(2R,3S,4R,5R)-4-Amino-5-(6-amino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol → 2'-amino-2'-deoxyadenosine (10414-81-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Yield given;

DOI:10.1021/ja962117m

upstream raw materials:

9-(2-acetamido-2-deoxy-3,5-diacetyl-β-D-ribofuranosyl)-6-chloropurine

adenine

1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil

4-tert-butyl-N-{9-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

Downstream raw materials:

2'-amino-2'-deoxyinosine

Refernces

• 1、 Ikehara,Maruyama,Miki. "Studies of nucleosides and nucleotides. LXXIV. Purine cyclonucleosides-34 a new method for the synthesis of 2-substituted 2'-deoxyadenosine". . p. 1133 - 1138. Retrieved 1978.
• 2、 Karpeisky, Alexander,Sweedler, David,Haeberli, Peter,Read, Javier,Jarvis, Keith,Beigelman, Leonid. "Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide synthesis.". . p. 3345 - 3347. Retrieved 2007/10/03.
• 3、 Utagawa, Takashi,Mirisawa, Hirokazu,Yamanaka, Shigeru,Yamazaki, Akihiro,Hirose, Yoshio. "Microbial Synthesis of Purine 2'-Amino-2'-deoxyribosides". . p. 2711 - 2718. Retrieved 2007/10/02.