Conditions | Yield |
---|---|
With pyridine; dmap; dimethyl sulfoxide In chloroform at 110℃; for 3h; | 97% |
With pyridine; dmap at 20℃; for 168h; | 96% |
Stage #1: succinic acid anhydride; cholesterol; dmap In 1,4-dioxane at 20℃; for 24h; Stage #2: With hydrogenchloride In 1,4-dioxane; water | 95% |
5-cholesten-3β-yl 2-(trimethylsilyl)ethyl butanedioate
cholesteryl hemisuccinate
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 2h; | 95% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 81% |
Conditions | Yield |
---|---|
Stage #1: cholesterol; succinoyl dichloride In acetonitrile at 50℃; for 12h; Stage #2: With hydrogenchloride In water; acetonitrile | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; benzene | |
With pyridine; toluene-4-sulfonic acid |
cholesterol
succinoyl dichloride
A
cholesteryl hemisuccinate
B
cholesteryl 3-succinate
Conditions | Yield |
---|---|
With benzene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / DCC, 4-dimethylaminopyridine / benzene / 5 h / 27 °C 2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 27 °C View Scheme |
cholesteryl hemisuccinate
cholesteryloxycarbonylpropionyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In toluene at 90℃; for 2h; | 100% |
With oxalyl dichloride In dichloromethane at 20℃; for 12h; | 98% |
With thionyl chloride In toluene at 80℃; for 1h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 75h; Reagent/catalyst; Solvent; | 96% |
Conditions | Yield |
---|---|
With pyridine; dmap; dimethyl sulfoxide In chloroform at 110℃; for 3h; | 97% |
With pyridine; dmap at 20℃; for 168h; | 96% |
Stage #1: succinic acid anhydride; cholesterol; dmap In 1,4-dioxane at 20℃; for 24h; Stage #2: With hydrogenchloride In 1,4-dioxane; water | 95% |
5-cholesten-3β-yl 2-(trimethylsilyl)ethyl butanedioate
cholesteryl hemisuccinate
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 27℃; for 2h; | 95% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 81% |
Conditions | Yield |
---|---|
Stage #1: cholesterol; succinoyl dichloride In acetonitrile at 50℃; for 12h; Stage #2: With hydrogenchloride In water; acetonitrile | 92% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; benzene | |
With pyridine; toluene-4-sulfonic acid |
cholesterol
succinoyl dichloride
A
cholesteryl hemisuccinate
B
cholesteryl 3-succinate
Conditions | Yield |
---|---|
With benzene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / DCC, 4-dimethylaminopyridine / benzene / 5 h / 27 °C 2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 27 °C View Scheme |
cholesteryl hemisuccinate
cholesteryloxycarbonylpropionyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In toluene at 90℃; for 2h; | 100% |
With oxalyl dichloride In dichloromethane at 20℃; for 12h; | 98% |
With thionyl chloride In toluene at 80℃; for 1h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 75h; Reagent/catalyst; Solvent; | 96% |
cholesteryl hemisuccinate
1-stearoyl-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 24h; | 90% |
cholesteryl hemisuccinate
5α,6β-dihydroxycholestan-3β-yl-hemisuccinate
Conditions | Yield |
---|---|
Stage #1: cholesteryl hemisuccinate With monoperoxyphthalic acid magnesium salt hexahydrate In acetone at 57℃; for 0.5h; Stage #2: With bismuth(lll) trifluoromethanesulfonate In acetone at 20℃; for 0.5h; | 90% |
1-hydroxy-pyrrolidine-2,5-dione
cholesteryl hemisuccinate
cholesterol-NHS ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at -10 - 20℃; for 4h; | 89% |
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide | |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1.5h; |
cholesteryl hemisuccinate
Ethyl-diisopropylphosphoramidochloridit
ethylene glycol
Conditions | Yield |
---|---|
at 20℃; for 10h; | 85.7% |
cholesteryl hemisuccinate
Conditions | Yield |
---|---|
dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 24h; Product distribution / selectivity; | 85% |
8-dioxane-3-cobalt-bis(1,2-dicarbollide)
cholesteryl hemisuccinate
potassium carbonate
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane for 6h; Reflux; | 83% |
Conditions | Yield |
---|---|
In chloroform at 38℃; for 8h; | 81% |
cholesteryl hemisuccinate
3,6,9,12,15,18-hexaoxa-1-octadecyl amine
N-{2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl}-succinamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 20h; | 80% |
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-propanol
cholesteryl hemisuccinate
A
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane
B
1,3-Dicyclohexylurea
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 6.08333h; Product distribution / selectivity; | A 79% B n/a |
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-propanol
cholesteryl hemisuccinate
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h; Product distribution / selectivity; | 79% |
cholesteryl hemisuccinate
5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; | 79% |
cholesteryl hemisuccinate
3-[N,N-bis(2-tert-butyldiphenylsilyloxyethyl)amino]-2-(tetradecanoyloxy)-1-[succinyloxy(4-cholesteryloxy)]propane
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6h; Cooling with ice; | 79% |
cholesteryl hemisuccinate
Conditions | Yield |
---|---|
Stage #1: cholesteryl hemisuccinate With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In acetonitrile at 81℃; for 0.583333h; Stage #2: (Bu4N)3{(MnMo6O18)3[(OCH2)3CNH2]2} In acetonitrile for 24h; Reflux; | 79% |
cholesteryl hemisuccinate
6A,6D-diamino-6A,6D-dideoxy-2A,D,3A,D-di-O-methylhexakis-(2A-G,3B-G,6B,C,E,F,G-tri-O-methyl)cyclomaltoheptaose
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 3h; | 78% |
cholesteryl hemisuccinate
7-ethyl-10-hydroxycamptothecin
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h; | 78% |
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; | 71.8% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 2.5h; | 70% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; | 75% |
2-methyl-2-propenoic acid 2-hydroxyethyl ester
cholesteryl hemisuccinate
2-(3-((cholesteryl)oxycarbonyl)propionyloxy)ethyl methacrylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; | 74% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 48h; | 72% |
cholesteryl hemisuccinate
mitomycin-C
3-(cholesteryloxycarbonyl)propanoyl MMC
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran; chloroform for 48h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 70% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h; | 70% |
4-{[(2-hydroxyethyl)(2-naphthylmethyl)amino]methyl}-N-(tetrahydro-2H-pyran-2-yloxy)benzamide
cholesteryl hemisuccinate
1-cholest-5-en-3-yl 4-{2-[(2-naphthylmethyl)(4-{[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl}benzyl)amino]ethyl} succinate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 65.8% |
4,6-diphenylthieno-[3,4-d]-1,3-dioxol-2-one-5,5-dioxide
cholesteryl hemisuccinate
Succinic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 1,1,4-trioxo-2,5-diphenyl-4,5-dihydro-1H-1λ6-thiophen-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 24h; | 64% |
cholesteryl hemisuccinate
ethylene glycol
Succinic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 2-hydroxy-ethyl ester
Conditions | Yield |
---|---|
Stage #1: cholesteryl hemisuccinate With thionyl chloride In toluene at 65℃; Stage #2: ethylene glycol With triethylamine In dichloromethane at 20℃; | 63% |
Stage #1: cholesteryl hemisuccinate With thionyl chloride In toluene Stage #2: ethylene glycol With triethylamine In dichloromethane at 20℃; |
The Cholesteryl hemisuccinate, with the CAS registry number 1510-21-0, is also known as Cholest-5-en-3beta-yl hydrogen succinate. It belongs to the product categories of Cholesteryl Compounds (Liquid Crystals); Functional Materials; Liquid Crystals & Related Compounds. Its EINECS registry number is 216-148-6. This chemical's molecular formula is C31H50O4 and molecular weight is 486.73. Its IUPAC name is called 4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid. This chemical is white powder.
Physical properties about Cholesteryl hemisuccinate are: (1)ACD/LogP: 10.32; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.19; (4)ACD/LogD (pH 7.4): 7.39; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 48165.85; (7)ACD/KOC (pH 5.5): 721507.88; (8)ACD/KOC (pH 7.4): 11509.87; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.528; (13)Molar Refractivity: 140.47 cm3; (14)Molar Volume: 455.5 cm3; (15)Surface Tension: 42.6 dyne/cm; (16)Density: 1.06 g/cm3; (17)Melting Point: 178 °C; (18)Flash Point: 179.6 °C; (19)Enthalpy of Vaporization: 95.62 kJ/mol; (20)Boiling Point: 586 °C at 760 mmHg; (21)Vapour Pressure: 2.99E-15 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC(=O)O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4
(2)InChI: InChI=1/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
(3)InChIKey: WLNARFZDISHUGS-MIXBDBMTBW
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