2',3',5'-Tri-O-acetyl-D-adenosine supplier

Name
2',3',5'-Tri-O-acetyl-D-adenosine
EINECS
CAS No. 7387-57-7
Article Data42
CAS DataBase
Density 1.62 g/cm³
Solubility
Melting Point 168-170°C
Formula C₁₆H₁₉N₅O₇
Boiling Point 594.1 °C at 760 mmHg
Molecular Weight 393.356
Flash Point 313.1 °C
Transport Information
Appearance White Solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2',3',5'-Tri-O-acetyladenosine;NSC 76766;Tri-O-acetyladenosine;
PSA 157.75000
LogP 0.31360

Synthetic route

: 108-24-7
acetic anhydride

: 58-61-7
adenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With pyridine for 6h; Ambient temperature;	96%
With dmap; triethylamine In acetonitrile at 20℃; for 24h;	96%
With pyridine Acetylation;	95%

: 58-61-7
adenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h; pH=8;	74%

: 3021-21-4
9-β-D-ribofuranosyl-6-thio-9H-purine 2',3',5'-triacetate

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With ammonia; oxygen; ozone In dichloromethane at 0℃; for 0.0833333h;	95%
With ammonia; 3,3-dimethyldioxirane In methanol; acetone at 25℃; for 4h;

: 3021-21-4
6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With ammonia; 3,3-dimethyldioxirane In dichloromethane; acetone at 25℃;	95%

: 88091-72-9
2',3',5'-tri-O-acetyl-N6-p-nitrophenylethoxycarbonyl adenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 18h; Ambient temperature;	92%
With 2,6-dichloro-benzonitrile; 1,8-diazabicyclo[5.4.0]undec-7-ene In pyridine

: 108-24-7
acetic anhydride

: 58-61-7
adenosine

A: 7387-58-8, 80007-24-5
6-N-2',3',5'-tri-O-tetraacetyladenosine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With dmap In pyridine at 20℃; for 24h; Cooling with ice;	A n/a B 50%
With pyridine at 20℃; Title compound not separated from byproducts;

...Expand

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

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With ammonia; 3,3-dimethyldioxirane In dichloromethane; acetone at 25℃;	53%

: 31199-61-8
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

A: 56787-20-3
2',3',5'-tri-O-acetyl-N6-methyl-adenosine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid at 40℃; for 1h;	A 32.3% B 48.1%

: 863591-77-9
6-pivaloylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
In methanol at 105℃; for 3h;	70%

: 71118-19-9
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(acetyl-ethyl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid for 0.5h; Ambient temperature;	83.2%

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 13035-61-5
1,2,3,5-tetraacetylribose

A: 906361-01-1
7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)adenine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Stage #1: adenine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 2.5h; Heating; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 1.33333h;	A 36% B 5.3%

...Expand

: 1574561-33-3
C16H21N7O7

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With water; oxygen; copper(II) sulfate at 80℃; for 6h; Green chemistry;	76%

: 80585-33-7
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-pyrrolidin-1-yl-purin-9-yl)-tetrahydro-furan-3-yl ester

A: 80585-36-0
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(2-oxo-pyrrolidin-1-yl)-purin-9-yl]-tetrahydro-furan-3-yl ester

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid at 40℃; for 1h;	A 48.2% B 4.3%

: 906361-01-1
7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)adenine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In chlorobenzene at 150℃; for 2.5h;

: 71138-53-9
2',3',5'-tri-O-acetyl-N6,N6-(diethyl)adenosine

A: 71118-19-9
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(acetyl-ethyl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid for 0.5h; Ambient temperature;	A 42.5% B 37.3%

: 80585-34-8
9-(2,3,5-tri-Ο-acetyl-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine

A: 80585-37-1
N-(2',3',5'-tri-O-acetyladenosin-6-yl)valeric acid

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid for 0.17h; Ambient temperature;	A 31.1% B 38.2%

: 154534-45-9
triethyl N-<9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purin-6-yl>phosphorimidate

A: 7387-57-7
triacetyladenosine

B: 154534-46-0
2',3',5'-tri-O-acetyladenosine 6-N-

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 96h; Ambient temperature;	A n/a B 51%

O2',O3',O5'-triacetyl-2-methylsulfanyl-adenosine: O2',O3',O5'-triacetyl-2-methylsulfanyl-adenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With ethanol; nickel at 110℃; under 7355.08 Torr; Hydrogenation;

: 31281-89-7
2',3',5'-tri-O-acetyl-8-iodoadenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With iodotrifluoromethane; copper In N,N,N,N,N,N-hexamethylphosphoric triamide at 110℃; for 40h;

: 23205-65-4
2',3',5'-tri-O-acetyl-8-aminoadenosine

A: 103904-90-1
8-amino-6-fluoro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With pyridine hydrogenfluoride; sodium nitrite In various solvent(s) 1.) -25 to -30 deg C, 1.5 h, 2.) 0 deg C, 15 min;

: 80585-32-6
N6,N6-Dibenzyl-2',3',5'-tri-O-acetyladenosine

A: 51549-18-9
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With potassium permanganate In water; acetic acid for 0.67h; Ambient temperature;	A 23.3% B 28.4%

: 7387-58-8, 80007-24-5
6-N-2',3',5'-tri-O-tetraacetyladenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
In methanol at 110℃; for 6h;

: 101-02-0
triphenyl phosphite

: 99148-16-0
6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

A: 78098-64-3
2',3',5'-tri-O-acetyl-N6-diphenylphosphoryladenosine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
In 1,4-dioxane for 4h; Heating;	A 78% B n/a

...Expand

: 13035-61-5
1,2,3,5-tetraacetylribose

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hexamethyldisilazane; (NH4)2SO4 / 2.5 h / Heating 1.2: 36 percent / trimethylsilyl triflate / acetonitrile / 1.33 h / 20 °C 2.1: p-toluenesulfonic acid monohydrate / chlorobenzene / 2.5 h / 150 °C View Scheme

: 53821-43-5
(2R,3R,4S,5R)-2-(6-azido-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / pyridine / Ambient temperature 2: dioxane / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 91 percent / pyridine / Ambient temperature 2: 96 percent / dioxane / 0.5 h / Ambient temperature 3: 0.01 M HCl / aq. ethanol / 96 h / Ambient temperature View Scheme

: 71138-53-9
2',3',5'-tri-O-acetyl-N6,N6-(diethyl)adenosine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 42.5 percent / KMnO4 / acetic acid; H2O / 0.5 h / Ambient temperature 2: 83.2 percent / KMnO4 / acetic acid; H2O / 0.5 h / Ambient temperature View Scheme

: 99148-16-0
6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / dioxane / 0.5 h / Ambient temperature 2: 0.01 M HCl / aq. ethanol / 96 h / Ambient temperature View Scheme

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 24 h / Reflux 2: copper(II) sulfate; water; oxygen / 6 h / 80 °C / Green chemistry View Scheme

: 2',3'-Bis-O-(methoxyacetyl)-6-N-(9-phenylxanthen-9-yl)adenosine 5'-phosphorodithioate O-(benzotriazol-1-yl) ester triethylammonium salt

: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. NaOH, 2.) aq. HCl / 1.) dioxane, r.t., 16 h, 2.) r.t., 40 min 2: 96 percent / pyridine / 6 h / Ambient temperature View Scheme

: 108-24-7
acetic anhydride

5'-O-acetyladenosine: 5'-O-acetyladenosine

A: 6554-24-1
3',5'-di-O-acetyladenosine

B: 7387-57-7
triacetyladenosine

Conditions

Conditions	Yield
With pyridine Erwaermen des Reaktionsprodukts mit wss.Essigsaeure;

...Expand

2',3',5'-Tri-O-acetyl-D-adenosine Specification

The 2',3',5'-Tri-O-acetyl-D-adenosine ,its cas register number is 7387-57-7.It also can be called as Adenosine,2',3',5'-triacetate and the IUPAC name about this chemicals is [3,4-Diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate .WGK Germany about this chemical is 3. If you want to store it, the temperature must below −20°C. It is a white solid. It belongs to the following product categories, such as Bases & Related Reagents, Nucleotides, Biochemicals and Reagents, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides and so on.

Following are the chemical properties about 2',3',5'-Tri-O-acetyl-D-adenosine :(1)#H bond acceptors: 12 ; (2)#H bond donors: 2 ; (3)#Freely Rotating Bonds: 8 ; (4)Polar Surface Area: 134.97Å² ; (5)Index of Refraction: 1.679 ; (6)Molar Refractivity: 91.22 cm³ ; (7)Molar Volume: 241.4 cm³ ; (8)Polarizability: 36.16x10^-24cm³ ; (9)Surface Tension: 62.7 dyne/cm ; (10)Enthalpy of Vaporization: 88.56 kJ/mol ; (11)Vapour Pressure: 4.41E-14 mmHg at 25°C

This chemical can be described computed from structure:
(1)Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)OC(=O)C)OC(=O)C
(2)InChI: InChI=1S/C16H19N5O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3,(H2,17,18,19)
(3)InChIKey: GCVZNVTXNUTBFB-UHFFFAOYSA-N

Product Name

2',3',5'-Tri-O-acetyl-D-adenosine

Synthetic route

2',3',5'-Tri-O-acetyl-D-adenosine Specification

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