Product Name

  • Name

    5'-Tosyladenosine

  • EINECS 225-883-1
  • CAS No. 5135-30-8
  • Article Data7
  • CAS DataBase
  • Density 1.75 g/cm3
  • Solubility
  • Melting Point 151-153 °C
  • Formula C17H19N5O6S
  • Boiling Point 760.1 °C at 760 mmHg
  • Molecular Weight 421.434
  • Flash Point 413.5 °C
  • Transport Information
  • Appearance white crystalline solid
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 5135-30-8 (5'-Tosyladenosine)
  • Hazard Symbols
  • Synonyms 5'-O-[(4-methylphenyl)sulfonyl]adenosine;Adenosine 5-(toluene-4-sulphonate);5-Tosyladenosine;adenosine 5'-(toluene-4-sulphonate);N-(5-diethylaminopentan-2-yl)-3-(3,4,5-trimethoxyphenyl)-2,5,10-triazabicyclo[4.4.0]deca-1,3,5,7,9-pentaene-7,9-diamine;adenosine, 5'-(4-methylbenzenesulfonate);
  • PSA 171.06000
  • LogP 1.40360

Synthetic route

5'-O-toluenesulphonyl-N6-benzoyladenosine
127246-72-4

5'-O-toluenesulphonyl-N6-benzoyladenosine

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Conditions
ConditionsYield
With ammonia In methanol Ambient temperature;720 mg
With ammonium hydroxide In methanol
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2.6-dioxy-4-methoxy-benzophenone

2.6-dioxy-4-methoxy-benzophenone

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aq. NH3 / methanol
View Scheme
N-benzoyladenosine
4546-55-8

N-benzoyladenosine

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aq. NH3 / methanol
View Scheme
Multi-step reaction with 2 steps
1: pyridine / Ambient temperature
2: 720 mg / ammonia / methanol / Ambient temperature
View Scheme
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / Ambient temperature
2: 720 mg / ammonia / methanol / Ambient temperature
View Scheme
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

N3,5'-cycloadenosine p-toluenesulfonate

N3,5'-cycloadenosine p-toluenesulfonate

Conditions
ConditionsYield
In ethanol for 3h; Heating;96%
2-trimethylsilylethanethiol
18143-30-1

2-trimethylsilylethanethiol

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5'-deoxy-5'-(2-(trimethylsilyl)ethyl)adenosine

5'-deoxy-5'-(2-(trimethylsilyl)ethyl)adenosine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 15h;96%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

8-bromo-5'-O-(p-tolylsulfonyl)adenosine
83316-88-5

8-bromo-5'-O-(p-tolylsulfonyl)adenosine

Conditions
ConditionsYield
With CH3COONa buffer; bromine In methanol for 0.5h; Ambient temperature;89%
N-(2-cyanoethyl)-N-methylamine
693-05-0

N-(2-cyanoethyl)-N-methylamine

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5'-<(2-cyanoethyl)methylamino>-5'-deoxyadenosine
72648-38-5

5'-<(2-cyanoethyl)methylamino>-5'-deoxyadenosine

Conditions
ConditionsYield
at 20℃; for 120h;87%
at 20℃; for 120h;87%
for 120h; Ambient temperature;80%
for 168h; Ambient temperature;42%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5'-deoxyadenosine
4754-39-6

5'-deoxyadenosine

Conditions
ConditionsYield
With lithium triethylborohydride In tetrahydrofuran for 1h; Ambient temperature;86%
With lithium triethylborohydride In tetrahydrofuran at 30℃; for 2h;23 mg
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Coβ-cyano-(adenin-7-yl)cobamide

Coβ-cyano-(adenin-7-yl)cobamide

Coβ-(5'-deoxy-5'-adenosyl)-(adenin-7-yl)cobamide

Coβ-(5'-deoxy-5'-adenosyl)-(adenin-7-yl)cobamide

Conditions
ConditionsYield
Stage #1: Coβ-cyano-(adenin-7-yl)cobamide With tert-butylammonium hexafluorophosphate(V); benzoic acid In methanol at 20℃; for 2h; Electrochemical reaction;
Stage #2: 5'-tosyladenosine In methanol at 20℃; for 2h; Electrochemical reaction;		84.7%
pseudovitamin B12

pseudovitamin B12

water
7732-18-5

water

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

coenzymeβ-(5'-deoxy-5'-adenosyl)-(adenin-7-yl)cobamide

coenzymeβ-(5'-deoxy-5'-adenosyl)-(adenin-7-yl)cobamide

Conditions
ConditionsYield
With benzoic acid In methanol Electrolysis; (N2); electrolysis (-1.1 V vs. 0.1 M calomel electrode) in presence of methanolic soln. of ((C4H9)4N)PF6 and benzoic acid at room temp. for 2 h,addn. of soln. of 5'-O-tosyladenosine in MeOH, electrolysis for 2 h in the dark under stirring; addn. of H2O, extn. with CH2Cl2, evapn. of aq. phase, dissolving in min.amt. of H2O, addn. of acetone, pptn. at 4°C overnight, washing w ith acetone, drying under vac., second pptn. by further addn. of acetone, chromy., drying in vac.;84.7%
...Expand
p-methoxybenzylmercaptan
6258-60-2

p-methoxybenzylmercaptan

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5′-deoxy-5′-(4-methoxybenzylthio)adenosine
595608-45-0

5′-deoxy-5′-(4-methoxybenzylthio)adenosine

Conditions
ConditionsYield
With N,N,N',N'-tetramethylguanidine for 0.25h; Inert atmosphere; Milling; Sealed tube;84%
tris(tetra-n-butylammonium) hydrogen pyrophosphate
76947-02-9

tris(tetra-n-butylammonium) hydrogen pyrophosphate

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

Conditions
ConditionsYield
In acetonitrile74%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

Conditions
ConditionsYield
With tris(tetra-n-butylammonium) hydrogen pyrophosphate In acetonitrile for 48h; Ambient temperature;74%
tris(tetrabutylammonium) salt of methylenebis(phosphonic acid)
93978-76-8

tris(tetrabutylammonium) salt of methylenebis(phosphonic acid)

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

O5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine
3768-14-7

O5'-(dihydroxyphosphorylmethyl-hydroxy-phosphinoyl)-adenosine

Conditions
ConditionsYield
In acetonitrile for 48h; Ambient temperature;72%
In acetonitrile for 48h;72%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

ATP
56-65-5

ATP

Conditions
ConditionsYield
With tetrakis(tetra-n-butylammonium) hydrogen triphosphate In acetonitrile for 48h; Ambient temperature;72%
tris(tetra-n-butylammonium) hydrogen difluoromethylenediphosphonate
104714-96-7

tris(tetra-n-butylammonium) hydrogen difluoromethylenediphosphonate

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

adenosine-5'-O-α,β-difluoromethylenediphosphate
107201-97-8

adenosine-5'-O-α,β-difluoromethylenediphosphate

Conditions
ConditionsYield
In dimethyl sulfoxide for 1h;65%
In acetonitrile for 66h;54%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3,4-bis-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3,4-bis-methanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
In pyridine for 5h;60%
tetrakis(tetra-n-butylammonium) hydrogen triphosphate
93978-77-9

tetrakis(tetra-n-butylammonium) hydrogen triphosphate

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

ATP
56-65-5

ATP

Conditions
ConditionsYield
In acetonitrile for 23h;55%
ethyleneimine
151-56-4

ethyleneimine

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine for 72h; Ambient temperature;24%
With N-ethyl-N,N-diisopropylamine at 20℃; for 72h;24%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

tris(tetrabutylammonium) salt of the monoacid of imidodiphosphate

tris(tetrabutylammonium) salt of the monoacid of imidodiphosphate

triethylammonium salt of AMPNP
114635-41-5, 119447-18-6

triethylammonium salt of AMPNP

Conditions
ConditionsYield
With imidodiphosphate; triethylamine carbonate In acetonitrile at 25℃; for 24h;22%
potassium selenocyanate
3425-46-5

potassium selenocyanate

5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5′-deoxyadenosinyl-5′-selenocyanate

5′-deoxyadenosinyl-5′-selenocyanate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 11h; Inert atmosphere; Milling;20%
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

tris(tetrabutylammonium) salt of the monoacid of imidodiphosphate

tris(tetrabutylammonium) salt of the monoacid of imidodiphosphate

5'-imidodiphosphate-Adenosine
32476-54-3

5'-imidodiphosphate-Adenosine

Conditions
ConditionsYield
With imidodiphosphate In acetonitrile at 25℃; for 24h;
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

ethylenediamine
107-15-3

ethylenediamine

5'-<(2-aminoethyl)amino>-5'-deoxyadenosine
81090-72-4

5'-<(2-aminoethyl)amino>-5'-deoxyadenosine

Conditions
ConditionsYield
for 168h; Ambient temperature;
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

Tributyl-amine; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Tributyl-amine; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Thiophosphoric acid S-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with tributyl-amine

Thiophosphoric acid S-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with tributyl-amine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given;
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5'-deoxy-5'-(thiocyanato)adenosine

5'-deoxy-5'-(thiocyanato)adenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / potassium carbonate / dimethylformamide / 15 h / 50 °C
2: 80 percent / methanol / 15 h / 20 °C
View Scheme
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

2',3'-didehydro-2',3'-dideoxyadenosine
7057-48-9

2',3'-didehydro-2',3'-dideoxyadenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / pyridine / 5 h
2: 55 percent / sodium naphthalenide / tetrahydrofuran / -50 °C
View Scheme
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

5'-deoxy-5'-thioadenosine-5'-triphosphate

5'-deoxy-5'-thioadenosine-5'-triphosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide / 24 h / Ambient temperature
2: 1.) N,N'-carbonyldiimidazole, n-Bu3N, 2.) methanol, tri-n-butylammonium pyrophosphate / 1.) DMF, rt, 4 h, 2.) DMF, rt, 20 h
View Scheme
5'-tosyladenosine
5135-30-8

5'-tosyladenosine

({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphoryl}-difluoro-methyl)-phosphonic acid

({[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphoryl}-difluoro-methyl)-phosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / dimethylsulfoxide / 1 h
2: CF3CO2H / dimethylsulfoxide
View Scheme

5'-Tosyladenosine Specification

The 5'-Tosyladenosine, with the CAS registry number 5135-30-8 and EINECS registry number 225-883-1, has the systematic name of 5'-O-[(4-methylphenyl)sulfonyl]adenosine. It is a kind of white crystalline solid, and belongs to the following product categories: API intermediates; Bases & Related Reagents; Nucleotides. And the molecular formula of the chemical is C17H19N5O6S. What's more, while dealing with this chemical, you should avoid contacting with skin and eyes. And it should be stored at -20°C.

The physical properties of 5'-Tosyladenosine are as followings: (1)ACD/LogP: 1.23; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.23; (4)ACD/LogD (pH 7.4): 1.23; (5)ACD/BCF (pH 5.5): 5.02; (6)ACD/BCF (pH 7.4): 5.08; (7)ACD/KOC (pH 5.5): 110.07; (8)ACD/KOC (pH 7.4): 111.39; (9)#H bond acceptors: 11; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 126.28 Å2; (13)Index of Refraction: 1.767; (14)Molar Refractivity: 99.77 cm3; (15)Molar Volume: 240.7 cm3; (16)Polarizability: 39.55×10-24cm3; (17)Surface Tension: 77.9 dyne/cm; (18)Density: 1.75 g/cm3; (19)Flash Point: 413.5 °C; (20)Enthalpy of Vaporization: 116.17 kJ/mol; (21)Boiling Point: 760.1 °C at 760 mmHg; (22)Vapour Pressure: 2.75E-24 mmHg at 25°C. 

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O)c4ccc(cc4)C
(2)InChI: InChI=1/C17H19N5O6S/c1-9-2-4-10(5-3-9)29(25,26)27-6-11-13(23)14(24)17(28-11)22-8-21-12-15(18)19-7-20-16(12)22/h2-5,7-8,11,13-14,17,23-24H,6H2,1H3,(H2,18,19,20)/t11-,13-,14-,17-/m1/s1
(3)InChIKey: CAXLRAROZXYOHH-LSCFUAHRBM

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