Everolimus supplier | CasNO.159351-69-6

Name
Everolimus
EINECS 621-003-9
CAS No. 159351-69-6
Article Data20
CAS DataBase
Density 1.18 g/cm³
Solubility Soluble in dimethysulfoxide,ethanol and chloroform. Slightly soluble in water.
Melting Point NA
Formula C₅₃H₈₃NO₁₄
Boiling Point 998.7 °C at 760 mmHg
Molecular Weight 958.24
Flash Point 557.8 °C
Transport Information
Appearance off white solid
Safety 45
Risk Codes 48/25
Molecular Structure
Hazard Symbols T
Synonyms 40-O-(2-Hydroxyethyl)rapamycin;42-O-(2-Hydroxy)ethylrapamycin;Certican;RAD;RAD 001;SDZ-RAD;XIENCE V;
PSA 204.66000
LogP 6.13510

Synthetic route

: 42-O-trityl-everolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water Solvent; Reagent/catalyst;	88%
With 1,1,1,3',3',3'-hexafluoro-propanol at 58℃; for 3.5h;

: 28-O-TES-42-O-THDMS everolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran at 0 - 10℃; for 1h;	71%
With sulfuric acid In tetrahydrofuran at 0 - 10℃; for 1h; Reagent/catalyst;	3.72 g

: 28-O-TMS-42-O-TBS everolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 0 - 5℃; for 1h;	68.3%
With hydrogenchloride In water; acetonitrile at -10 - 0℃; for 0.5h;	20.4 g
With hydrogenchloride In acetone at 0 - 5℃; for 1h;	3.58 g

: 42-O-[2-(1-methyl-1-methoxyethoxy)ethyl]rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 5℃; pH=3 - 4;	68%

: 42-O-[2(tetrahydrofuran-2-oxy)ethyl]rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 5℃;	67%

: 42-O-[2-(1-ethoxyethoxy)ethyl]rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 5℃;	65%

: 42-O-[2(tetrahydro-2H-furan-2-oxy)ethyl]rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 5℃;	61%

: 42-O-[2-(methoxymethoxy)ethyl]rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 5℃;	55%

: 159351-68-5
40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With triethylamine tris(hydrogen fluoride) In tetrahydrofuran at 20℃; for 2h;	54%
With pyridine hydrogenfluoride In tetrahydrofuran at 0 - 45℃; for 1.5h;	2.96 g
With hydrogenchloride In methanol; water at 0 - 25℃; for 1h; pH=1-3; pH-value; Time;

: 1314705-20-8
40-O-[2-(t-butyldiphenylsilyl)oxy]ethyl-rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With pyridine; hydrogen fluoride In tetrahydrofuran at 0 - 20℃; for 4h;	15%
With pyridine hydrogenfluoride In tetrahydrofuran at 0 - 20℃; for 4h;	15%
With pyridine hydrogenfluoride In tetrahydrofuran at 0 - 45℃; for 3.5h; Temperature;	6.81 g
With hydrogenchloride In water; acetonitrile at -10 - 0℃; for 0.5h;

: 1392400-31-5
40-O-[2-((2,3-dimethylbut-2-yl)dimethylsilyloxy)ethyl] rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 0℃; for 1.5h;
With hydrogenchloride In methanol; water at -10℃; Inert atmosphere;

: C74H101NO16

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; for 1.5h; Reagent/catalyst;	621 mg

: 53123-88-9
sirolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (1-ethylpropyl)diisopropylamine / toluene / 30 °C 2: pyridine hydrogenfluoride / tetrahydrofuran / 3.5 h / 0 - 45 °C View Scheme
Multi-step reaction with 2 steps 1.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -40 °C 1.2: -40 - 40 °C 2.1: hydrogenchloride / methanol; water / 1 h / 0 - 25 °C / pH 1-3 View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / toluene / 12 h / 60 °C 2: hydrogenchloride / methanol; water / 5 °C View Scheme

: 40-O-[2-(triisopropylsilyl)oxy]ethyl-rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride; phosphoric acid; water In n-heptane; acetonitrile at 20℃; for 24h;	64 %Chromat.

: 331810-13-0
31,42-bis(trimethylsilylether)rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / tetrahydrofuran / 5 h / Cooling with ice 2: hydrogenchloride / toluene; water / 6 h / 0 - 10 °C 3: hydrogenchloride / water; methanol / 4.5 h / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / ethyl acetate; water / Cooling with ice 2: N-ethyl-N,N-diisopropylamine / 1,2-dimethoxyethane; toluene / 4 h / 60 °C 3: hydrogenchloride / water; acetone / 1 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / Cooling with ice 2: N-ethyl-N,N-diisopropylamine / toluene; 1,2-dimethoxyethane / 4 h / 60 °C 3: hydrogenchloride / acetone / 1 h / 0 - 5 °C View Scheme

: C56H91NO14Si

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 4.5h; Cooling with ice;	3.8 g

: 75-21-8
oxirane

: 53123-88-9
sirolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 70℃; under 7500.75 Torr; for 8h; Reagent/catalyst; Temperature; Pressure; Solvent; Autoclave;	6.9 g

: 107-21-1
ethylene glycol

: 53123-88-9
sirolimus

: 159351-69-6
everolimus

Conditions

Conditions	Yield
Stage #1: ethylene glycol With trifluoroacetic anhydride In tetrahydrofuran at 10℃; for 1.5h; Inert atmosphere; Large scale; Stage #2: sirolimus With boron trifluoride diethyl etherate In tetrahydrofuran at 10℃; for 2h; Temperature; Large scale;	5.7 kg

: C56H91NO14Si

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at -10 - 0℃; for 0.5h;

: C59H97NO14Si

: 159351-69-6
everolimus

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at -10 - 0℃; for 0.5h;

: 331810-10-7
31-(trimethylsilylether)rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 1,2-dimethoxyethane; toluene / 4 h / 60 °C 2: hydrogenchloride / water; acetone / 1 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / toluene; 1,2-dimethoxyethane / 4 h / 60 °C 2: hydrogenchloride / acetone / 1 h / 0 - 5 °C View Scheme

: 155435-45-3
31,42-bis(triethylsilylether)rapamycin

: 159351-69-6
everolimus

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / acetone / 0 - 10 °C 2: N-ethyl-N,N-diisopropylamine / toluene / 4 h / 53 °C 3: sulfuric acid / tetrahydrofuran / 1 h / 0 - 10 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / acetone / 0 - 10 °C 2: N-ethyl-N,N-diisopropylamine / toluene; hexane / 2 h / 60 °C 3: sulfuric acid / tetrahydrofuran / 1 h / 0 - 10 °C View Scheme

: 5309-70-6
vinyl bromoacetate

: 159351-69-6
everolimus

: 159351-81-2
everolimus 42-bromoacetate

Conditions

Conditions	Yield
Novozym 435TM lipase In tert-butyl methyl ether at 35℃; for 10h; Molecular sieve;	96%
at 20℃; for 4h; Enzymatic reaction;

: 159351-69-6
everolimus

: 1422173-29-2
42-O-(2-fluoroethyl)rapamycin

Conditions

Conditions	Yield
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 5h; Inert atmosphere;	83%

: 64-69-7
Iodoacetic acid

: 159351-69-6
everolimus

: SDZ-RAD-iodoacetate ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; Darkness;	73%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.66667h;

: 2-{[tert-butyl(diphenyl)silyl]oxy}ethyl trifluoromethansulphonate

: 159351-69-6
everolimus

: (35E,37E,39E,40E,48R,49S,50R,51R,53S,55S,57S,58S,59R,60R,69R)-58-[(1R)-2-[(1S,3R,4R)-4-[2-[2-[tert-butyl(diphenyl)silyl]oxyethoxy]ethoxy]-3-methoxy-cyclohexyl]-1-methyl-ethyl]-59,69-dihydroxy-57,60-dimethoxy-48,49,50,51,61,62-hexamethyl-79,80-dioxa-71-azatricyclohexatriaconta-35,37,39(61),40(62)-tetraene-63,64,65,66,67-pentone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 45℃; for 18h;	59%

: 159351-69-6
everolimus

: C53H83NO14

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 60℃; for 2h; Reagent/catalyst;	45%

: 159351-69-6
everolimus

: (22E,24E,26E,27E,31R,32S,33R,34R,36S,38S,40S,41S,42S,43R,52R)-42,52-dihydroxy-41-[(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-40,43-dimethoxy-31,32,33,34,44,45-hexamethyl-62,63-dioxa-53-azatricyclohexatriaconta-22,24,26(44),27(45)-tetraene-46,47,48,49,50-pentone

Conditions

Conditions	Yield
With titanium(IV) isopropylate In dichloromethane at 20℃;	38%

: 159351-69-6
everolimus

: 112-27-6
2,2'-[1,2-ethanediylbis(oxy)]bisethanol

: (21E,23E,25E,26E,36R,37S,38R,39R,41S,43S,46S,47R,48R,57R)-47,57-dihydroxy-45-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-46-[(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-48-methoxy-36,37,38,39,49,50-hexamethyl-68,69-dioxa-58-azatricyclohexatriaconta-21,23,25(49),26(50)-tetraene-51,52,53,54,55-pentone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; water at 20℃; for 2h;	28%

: 159351-69-6
everolimus

: 111-46-6
diethylene glycol

: (21E,23E,25E,26E,34R,35S,36R,37R,39S,41S,44S,45R,46R,55R)-45,55-dihydroxy-43-[2-(2-hydroxyethoxy)ethoxy]-44-[(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-46-methoxy-34,35,36,37,47,48-hexamethyl-66,67-dioxa-56-azatricyclohexatriaconta-21,23,25(47),26(48)-tetraene-49,50,51,52,53-pentone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; water at 20℃; for 2h;	19%

: 112-60-7
Tetraethylene glycol

: 159351-69-6
everolimus

: (21E,23E,25E,26E,38R,39S,40R,41R,43S,45S,48S,49R,50R,59R)-49,59-dihydroxy-47-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]-48-[(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-50-methoxy-38,39,40,41,51,52-hexamethyl-70,71-dioxa-60-azatricyclohexatriaconta-21,23,25(51),26(52)-tetraene-53,54,55,56,57-pentone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; water at 20℃; for 2h;	17%

: 5617-32-3
heptaethylene glycol

: 159351-69-6
everolimus

: (21E,23E,25E,26E,44R,45S,46R,47R,49S,51S,54S,55R,56R,65R)-55,65-dihydroxy-53-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-54-[(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-56-methoxy-44,45,46,47,57,58-hexamethyl-76,77-dioxa-66-azatricyclohexatriaconta-21,23,25(57),26(58)-tetraene-59,60,61,62,63-pentone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; water at 22℃; for 18h; Inert atmosphere;	14%

: 159351-69-6
everolimus

: 40-O-(2-hydroxy)ethyl rapamycin

Conditions

Conditions	Yield
With triethylammonium acetate In 1,4-dioxane; water at 22 - 28℃; for 4h;

: 913168-10-2
1H-benzo[d][1,2,3]triazol-1-yl (2-(pyridin-2-yldisulfaneyl)ethyl) carbonate

: 159351-69-6
everolimus

: 1312678-90-2
everolimus (2'-pyridyldisulfanyl)ethyl carbonate

Conditions

Conditions	Yield
With dmap In dichloromethane for 0.5h; Inert atmosphere;

: 141-82-2
malonic acid

: 159351-69-6
everolimus

: C54H83NO15

Conditions

Conditions	Yield
In methanol at 20℃; for 10h;

Everolimus Specification

The Everolimus is an organic compound with the formula C₅₃H₈₃NO₁₄. With the CAS registry number 159351-69-6, it is also named as Certican. The product's categories are All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is an off white aolid, which should be stored at temperature of -20 °C. Everolimus is used in drug-eluting coronary stents as an immunosuppressant to prevent restenosis.

Physical properties about Everolimus are: (1)ACD/LogP: 3.35; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.35; (4)ACD/LogD (pH 7.4): 3.35; (5)#H bond acceptors: 15; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 12; (8)Polar Surface Area: 204.66 Å²; (9)Index of Refraction: 1.548; (10)Molar Refractivity: 257.69 cm³; (11)Molar Volume: 811.2 cm³; (12)Polarizability: 102.15×10^-24cm³; (13)Surface Tension: 51.3 dyne/cm; (14)Density: 1.18 g/cm³; (15)Flash Point: 557.8 °C; (16)Enthalpy of Vaporization: 165.09 kJ/mol; (17)Boiling Point: 998.7 °C at 760 mmHg.

When you are using this chemical, please be cautious about it as the following:
This chemical is danger of serious damage to health by prolonged exposure if swallowed. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: OCCO[C@@H]1CC[C@H](C[C@H]1OC)C[C@@H](C)[C@@H]4CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(/C)[C@@H](OC)C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N3CCCC[C@H]3C(=O)O4
(2)InChI: InChI=1/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1
(3)InChIKey: HKVAMNSJSFKALM-GKUWKFKPBE
(4)Std. InChI: InChI=1S/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1
(5)Std. InChIKey: HKVAMNSJSFKALM-GKUWKFKPSA-N

Product Name

Everolimus

Synthetic route

Everolimus Specification

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