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C33H45NO4S
cyclopamine
Conditions | Yield |
---|---|
Stage #1: C33H45NO4S With naphthalene; sodium In 1,2-dimethoxyethane at -78℃; for 3h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In 1,2-dimethoxyethane at -78 - 20℃; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate Heating; 1.) triethylene glycol, 120 deg C, 1 h, 2.) triethylene glycol, 200 deg C, 3 h; | 51% |
With sodium; hydrazine In diethylene glycol Heating; |
Conditions | Yield |
---|---|
With water at 37℃; pH=7; aq. phosphate buffer; Inert atmosphere; |
Conditions | Yield |
---|---|
With b-glucuronidase from E. Coli at 37℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction; |
cyclopamine
Conditions | Yield |
---|---|
With water; 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol; dimethyl sulfoxide at 37℃; for 22h; pH=7.2; pH-value; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction; |
cyclopamine
Conditions | Yield |
---|---|
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux; | 99% |
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux; Inert atmosphere; | 85% |
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux; | 70% |
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux; | 70% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Heating; | 94% |
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Reflux; | 94% |
Conditions | Yield |
---|---|
With dmap; triethylamine In 1-Propyl acetate at 20℃; for 4h; Inert atmosphere; Large scale; | 91.8% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; | 85% |
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 20h; | 85% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; | 85% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
cyclopamine
Fmoc-cyclopamine
Conditions | Yield |
---|---|
In dichloromethane at 23℃; for 64h; Inert atmosphere; | 81% |
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; | 80% |
cyclopamine
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-nitro-4-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
C48H62N2O16
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
Stage #1: C9H14O5 With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Stage #2: cyclopamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; | 76% |
2-(2,2,2-trifluoroacetamido)acetic acid succinimidyl ester
cyclopamine
N-(N'-trifluoroacetylglycyl)cyclopamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 60% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 15℃; for 16h; | 56.33% |
With triethylamine In dichloromethane at 20℃; for 0.166667h; | 51% |
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With pyridine at 60℃; for 18h; | 80 % Spectr. |
cyclopamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent Spectr. / pyridine / 18 h / 60 °C 2: 1,3-dicyclohexylcarbodiimide / CHCl3 / 16 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 70℃; for 36h; |
Conditions | Yield |
---|---|
With triethylamine In methanol; dichloromethane at 0℃; for 3.5h; | |
With triethylamine In methanol; dichloromethane for 3.5h; Cooling with ice; |
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 40℃; for 2h; Product distribution / selectivity; | |
With dmap; triethylamine In methanol; ethyl acetate at 40℃; for 18h; Product distribution / selectivity; |
cyclopamine
1-benzyloxycarbonyloxy-1H-benzotriazole
bis-CBz-cyclopamine
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 40℃; for 2h; | |
With pyridine; dmap; triethylamine at 40℃; for 2h; |
Conditions | Yield |
---|---|
In methanol |
cyclopamine
C32H52N2O5
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C34H56N2O5
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
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