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Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)-
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Name

Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)-

 EINECS N/A
CAS No. 115375-60-5 Density 1.407 g/cm3
PSA 78.05000 LogP 6.32170
Solubility N/A Melting Point N/A
Formula C22H29F3O5S Boiling Point 491.88 °C at 760 mmHg
Molecular Weight 462.53 Flash Point 251.28 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 115375-60-5 ((3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(Trifluoromethanesulfonate)) Hazard Symbols N/A
Synonyms

[(3S,10R,13S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;(3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(trifluoromethanesulfonate);

Article Data 28

Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)- Synthetic route

358-23-6

trifluoromethylsulfonic anhydride

853-23-6

prasterone acetate

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h;
Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h; Reagent/catalyst; Solvent; Temperature;		96%
Stage #1: prasterone acetate With potassium carbonate In toluene; benzene at 25℃; for 0.5h;
Stage #2: trifluoromethylsulfonic anhydride In toluene; benzene at -18 - -15℃; for 20.33h;		96%
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With 2-methoxypyridine In dichloromethane at 20 - 30℃; for 2.5h; Reagent/catalyst;		93%
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

853-23-6

prasterone acetate

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
Stage #1: prasterone acetate With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 2h;		85%
Stage #1: prasterone acetate With potassium hexamethylsilazane In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran for 8h; Inert atmosphere;		70%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -80 - 0℃; for 4h;850 mg
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -80 - 5℃; for 2.5h;64.8 g
358-23-6

trifluoromethylsulfonic anhydride

853-23-6

prasterone acetate

A

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

B

154229-36-4

androsta-3,5,16-trien-17-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 12h;A 58%
B 10%
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 3 - 16h; Product distribution / selectivity;
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate With 2,6-dimethylpyridine In ethyl acetate for 0.25h;
Stage #2: With 2,6-dimethylpyridine In ethyl acetate for 2h; Product distribution / selectivity;
358-23-6

trifluoromethylsulfonic anhydride

853-23-6

prasterone acetate

A

53-43-0

dehydroepiandrosterone

B

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In 2-Methylpentane for 0.25h;
Stage #2: With triethylamine In 2-Methylpentane for 2h; Product distribution / selectivity;
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In ethyl acetate for 0.25h;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate for 2h; Product distribution / selectivity;
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In 1,2-dichloro-ethane for 0.25h;
Stage #2: With sodium hydride In 1,2-dichloro-ethane for 2h; Product distribution / selectivity;
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate for 0.25h;
Stage #2: With triethylamine for 2h; Product distribution / selectivity;
358-23-6

trifluoromethylsulfonic anhydride

853-23-6

prasterone acetate

A

53-43-0

dehydroepiandrosterone

B

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

C

154229-36-4

androsta-3,5,16-trien-17-yl trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In dichloromethane for 0.25h;
Stage #2: With pyridine In dichloromethane for 2h; Product distribution / selectivity;
Stage #1: trifluoromethylsulfonic anhydride; prasterone acetate In ethyl acetate for 0.25h;
Stage #2: With pyridine In ethyl acetate for 2h; Product distribution / selectivity;
53-43-0

dehydroepiandrosterone

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 2 h / 105 - 110 °C / Inert atmosphere
2.1: potassium carbonate / toluene; benzene / 0.5 h / 25 °C
2.2: 20.33 h / -18 - -15 °C
View Scheme
Multi-step reaction with 2 steps
1.1: pyridine; dmap / 0.25 h / 20 °C
1.2: 6 h / 20 °C
2.1: triethylamine / dichloromethane / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: pyridine / 20 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C
2.2: 2 h / -78 °C
View Scheme
853-23-6

prasterone acetate

145100-50-1

1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -80 - -70℃; for 2h; Reagent/catalyst; Large scale;112 kg
115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

89878-14-8

3-Diethylboranylpyridine

154229-18-2

abiraterone acetate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 65℃; for 4h; Reflux;95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 1h; Reflux;95%
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 1h;94%
115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

98-80-6

phenylboronic acid

76208-39-4

17-phenylandrosta-5,6-dien-3β-ol 3-acetate

Conditions
ConditionsYield
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry;
Stage #2: phenylboronic acid With sodium carbonate In water at 75℃; Catalytic behavior; Reagent/catalyst; Time; Suzuki Coupling; Inert atmosphere; Green chemistry;		92%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 100℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere;85%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In toluene at 20 - 100℃; for 6.08333h; Inert atmosphere;85%
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 23h; Suzuki Coupling; Inert atmosphere;70%
850991-69-4

5-methoxy-3-pyridinylboronic acid

115375-60-5

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

3β-acetoxy-17-(5-methoxylpyridin-3-yl)androsta-5,16-diene

Conditions
ConditionsYield
Stage #1: 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate With copper(l) iodide; palladium dichloride In water at 20℃; for 0.0833333h; Suzuki Coupling; Inert atmosphere; Green chemistry;
Stage #2: 5-methoxy-3-pyridinylboronic acid With sodium carbonate In water at 75℃; Suzuki Coupling; Inert atmosphere; Green chemistry;		88%

Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)- Specification

The Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)-, with the CAS registry number 115375-60-5, is also known as (3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(trifluoromethanesulfonate). This chemical's molecular formula is C22H29F3O5S and molecular weight is 462.52. What's more, its systematic name is [(3S,10R,13S)-10,13-dimethyl-17-(trifluoromethylsulfonyloxy)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate.

Physical properties of Androsta-5,16-diene-3,17-diol, 3-acetate 17-(trifluoromethanesulfonate), (3β)- are: (1)ACD/LogP: 1.77; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.57; (4)ACD/LogD (pH 7.4): -1.86; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.01; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 57.65 Å2; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 73.14 cm3; (15)Molar Volume: 221.4 cm3; (16)Polarizability: 28.99×10-24cm3; (17)Surface Tension: 50.7 dyne/cm; (18)Density: 1.407 g/cm3; (19)Flash Point: 201.9 °C; (20)Enthalpy of Vaporization: 69.85 kJ/mol; (21)Boiling Point: 410.2 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)O[C@H]1CC[C@@]2(C3CC[C@]4(C(C3CC=C2C1)CC=C4OS(=O)(=O)C(F)(F)F)C)C
(2)InChI: InChI=1S/C22H29F3O5S/c1-13(26)29-15-8-10-20(2)14(12-15)4-5-16-17-6-7-19(21(17,3)11-9-18(16)20)30-31(27,28)22(23,24)25/h4,7,15-18H,5-6,8-12H2,1-3H3/t15-,16?,17?,18?,20-,21-/m0/s1
(3)InChIKey: MCIVSCZCJRGEJR-KJBVPOJVSA-N

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