Name: 2-Azidoadenosine
SKU: 59587-07-4

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Basic Information

Molecular Structure:
CAS No.:	59587-07-4
Name:	2-Azidoadenosine
Article Data:	5

Formula:	C₁₀H₁₂N₈O₄
Molecular Weight:	308.256
Synonyms:	2-Azido-D-adenosine;(4S,2R,3R,5R)-2-[6-Amino-2-(diazoazamvinyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol;NSC 36905;AC1LABXO;(2R,3R,4S,5R)-2-(6-Amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;
Melting Point:	170-172 °C
Appearance:	Off-white to grey solid
PSA:	189.29000
LogP:	-1.00424

Synthetic route

: 174500-37-9
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
With ammonia In ethanol at 30℃; for 48h;	89%

: 146-77-0
2-Chloroadenosine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Stage #1: 2-Chloroadenosine With hydrazine hydrate at 20℃; for 16h; Stage #2: With acetic acid; sodium nitrite In water for 1h; cooling;	61%
Multi-step reaction with 2 steps 1: H2NNH2*H2O / 20 °C 2: NaNO2; acetic acid / H2O / 0 °C View Scheme

2-hydrazono-adenosine: 2-hydrazono-adenosine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
With acetic acid; sodium nitrite

: 15763-11-8
2-hydrazinoadenosine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In water at 0℃;

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin: thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

: 15373-23-6
(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NH3 / methanol / 20 °C 2.1: hydrazine monohydrate / 16 h / 20 °C 2.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

: 5451-40-1
2,6 dichloropurine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

: 16321-99-6
2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 2: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

: 118-00-3
G

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / dimethylformamide 2: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 3: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 4: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

: 6979-94-8
2',3',5'-tri-O-acetyl-guanosine

: 59587-07-4
2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 2: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 3: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

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Specification

The Adenosine, 2-azido- with CAS registry number of 59587-07-4 is also known as 2-Azidoadenosine. The IUPAC name is (2R,3R,4S,5R)-2-(6-Amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol. It belongs to product categories of Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides. In addition, the formula is C₁₀H₁₂N₈O₄ and the molecular weight is 308.25. What's more, this chemical is a off-white to grey solid and it is used as synthetic intermediate for making potent and selective coronary vasodilators.

Physical properties about Adenosine, 2-azido- are: (1)ACD/LogP: -3.22; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3.22; (4)ACD/LogD (pH 7.4): -3.22; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 96.12Å².

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)CO)O)O)N=C(N=C2N)N=[N+]=[N-]
2. Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(N=C2N)N=[N+]=[N-]
3. InChI: InChI=1S/C10H12N8O4/c11-7-4-8(15-10(14-7)16-17-12)18(2-13-4)9-6(21)5(20)3(1-19)22-9/h2-3,5-6,9,19-21H,1H2,(H2,11,14,15)/t3-,5-,6-,9-/m1/s1
4. InChIKey: BSZZPOARGMTJKQ-UUOKFMHZSA-N