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miglustat hydrochloride
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene | 99.5% |
N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
With ammonia; lithium In tetrahydrofuran at -78℃; for 2.5h; | 91% |
With boron trichloride In hexane; dichloromethane at -78℃; | 83% |
With 10 wt% Pd(OH)2 on carbon; hydrogen In ethanol; chloroform at 20℃; for 20h; | |
With hydrogenchloride; 16% Pd/C; hydrogen In methanol; water under 3000.3 Torr; for 4h; | 50 g |
With hydrogenchloride; 16% Pd/C; hydrogen In methanol; water under 3000.3 Torr; for 4h; | 50 g |
1-bromo-butane
1,5-dideoxy-1,5-imino-D-glucitol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; for 24h; | 76% |
With sodium hydrogencarbonate In 1,4-dioxane; methanol for 48h; Heating; | |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; |
1,5-dideoxy-1,5-imino-D-glucitol
butyraldehyde
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; under 2585.81 Torr; | 60% |
palladium In methanol | |
palladium In methanol |
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In methanol 1.) -78 deg C, 2 h, 2.) r.t., 20 h; | A 55% B 10% |
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Stage #1: C24H33NO4 With trimethylsilyl iodide In dichloromethane at 20℃; for 0.25h; Stage #2: With methanol In dichloromethane | 33% |
2,3,4,6-tetra-O-benzyl-D-glucopyranose
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 2: 1.) TFAA, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1.5 h, 2.) CH2Cl2, -78 deg C to r.t., 30 min 3: 77 percent / NaBH3CN, molecular sieves 3 Angstroem / methanol / 0.5 h / Ambient temperature 4: 91 percent / Li, NH3 / tetrahydrofuran / 2.5 h / -78 °C View Scheme |
2,3,4,6-tetra-O-benzyl-D-glucitol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) TFAA, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1.5 h, 2.) CH2Cl2, -78 deg C to r.t., 30 min 2: 77 percent / NaBH3CN, molecular sieves 3 Angstroem / methanol / 0.5 h / Ambient temperature 3: 91 percent / Li, NH3 / tetrahydrofuran / 2.5 h / -78 °C View Scheme | |
Multi-step reaction with 6 steps 1: pyridine / dichloromethane / 20 °C / Inert atmosphere 2: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere 3: sodium methylate / methanol / 5 h / 20 °C 4: pyridine / 5 h / 20 °C 5: 96 h / 55 °C 6: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 4 h / 50 °C / Inert atmosphere 2: sodium cyanoborohydride; sodium sulfate; acetic acid / dichloromethane; methanol / 15 h / 20 °C / pH 6 / Inert atmosphere 3: hydrogenchloride; 16% Pd/C; hydrogen / methanol; water / 4 h / 3000.3 Torr View Scheme |
(2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / NaBH3CN, molecular sieves 3 Angstroem / methanol / 0.5 h / Ambient temperature 2: 91 percent / Li, NH3 / tetrahydrofuran / 2.5 h / -78 °C View Scheme |
1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / Dowex 50W-X8 / H2O / 36 h / 25 °C 2: 55 percent / HOAc, NaBH3CN / methanol / 1.) -78 deg C, 2 h, 2.) r.t., 20 h View Scheme |
1,2-O-isopropylidene-α-D-glucofuranose
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) dibutylin oxide hemihydrate, 2.) Br2 / 1.) MeOH, reflux, 1.5 h, 2.) CH2Cl2, 0 deg C, 10 min 2: 70 percent / Dowex 50W-X8 / H2O / 36 h / 25 °C 3: 55 percent / HOAc, NaBH3CN / methanol / 1.) -78 deg C, 2 h, 2.) r.t., 20 h View Scheme |
2,2-dimethylpropanoic anhydride
N-butyldeoxynojirimycin
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 h / 55 °C 2: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme |
(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C 3: pyridine / 5 h / 20 °C 4: 96 h / 55 °C 5: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme |
(2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium methylate / methanol / 5 h / 20 °C 2: pyridine / 5 h / 20 °C 3: 96 h / 55 °C 4: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: sodium tetrahydroborate / ethanol / 12 h / Inert atmosphere 2: pyridine / dichloromethane / 20 °C / Inert atmosphere 3: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere 4: sodium methylate / methanol / 5 h / 20 °C 5: pyridine / 5 h / 20 °C 6: 96 h / 55 °C 7: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: acetic anhydride; dimethyl sulfoxide / 20 °C 2: ammonia / methanol / 3 h / 0 °C 3: acetic anhydride; dimethyl sulfoxide / 6 h / 20 °C 4: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 6: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 7: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
(2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / 5 h / 20 °C 2: 96 h / 55 °C 3: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol; chloroform / 20 h / 20 °C View Scheme |
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
With 4% Pd/C; hydrogen In water at 20℃; under 3345.86 Torr; for 2.33333h; pH=5; |
2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosononitrile
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium hydroxide, 20 wt% on carbon; hydrogen / tert-butyl alcohol; methanol / 25 °C / 7757.43 - 8791.75 Torr 1.2: 0.5 h 1.3: 4654.46 - 5171.62 Torr 2.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 - 90 °C View Scheme |
methyl-alpha-D-glucopyranoside
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: sodium hydride / N,N-dimethyl-formamide / 8 h / 0 - 20 °C 2: acetic acid; sulfuric acid / Reflux 3: acetic anhydride; dimethyl sulfoxide / 20 °C 4: ammonia / methanol / 3 h / 0 °C 5: acetic anhydride; dimethyl sulfoxide / 6 h / 20 °C 6: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 7: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 8: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 9: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 3: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 4: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: acetic acid; sulfuric acid / Reflux 2: acetic anhydride; dimethyl sulfoxide / 20 °C 3: ammonia / methanol / 3 h / 0 °C 4: acetic anhydride; dimethyl sulfoxide / 6 h / 20 °C 5: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 6: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 7: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 8: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: ammonia / methanol / 3 h / 0 °C 2: acetic anhydride; dimethyl sulfoxide / 6 h / 20 °C 3: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 4: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 5: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 6: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
2,3,4,6-tetra-O-benzyl-D-gluconamide
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetic anhydride; dimethyl sulfoxide / 6 h / 20 °C 2: sodium cyanoborohydride; formic acid / acetonitrile / 3 h / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 4: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 5: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 2: potassium carbonate / acetonitrile / 24 h / Reflux; Inert atmosphere 3: boron trichloride / dichloromethane; hexane / -78 °C View Scheme |
2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium on carbon; hydrogen; hydrogenchloride / ethanol; water / 24 h / 3000.3 Torr / pH 2 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 70 °C / Inert atmosphere View Scheme |
3,4-di-O-benzyl-D-mannitol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 0 °C 2: triethylamine / dichloromethane 3: hydrogenchloride; methanol 4: sodium hydroxide / water 5: methanol / 0.08 h / 90 °C / Microwave irradiation; Sealed tube 6: trimethylsilyl iodide / dichloromethane / 0.25 h / 20 °C View Scheme |
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,5-diol
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane 2: hydrogenchloride; methanol 3: sodium hydroxide / water 4: methanol / 0.08 h / 90 °C / Microwave irradiation; Sealed tube 5: trimethylsilyl iodide / dichloromethane / 0.25 h / 20 °C View Scheme |
Methanesulfonic acid (1R,2S,3S,4R)-2,3-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methanesulfonyloxy-pentyl ester
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride; methanol 2: sodium hydroxide / water 3: methanol / 0.08 h / 90 °C / Microwave irradiation; Sealed tube 4: trimethylsilyl iodide / dichloromethane / 0.25 h / 20 °C View Scheme |
N-butyldeoxynojirimycin
1,5-(Butylimino)-1,5-dideoxy-D-glucitol, 6-acetate
Conditions | Yield |
---|---|
With acetic anhydride In pyridine; water | |
With acetic anhydride In pyridine; water | |
With acetic anhydride In pyridine; water | |
With acetic anhydride In pyridine; water |
p-toluenesulfonic acid monohydrate
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
In N-methyl-acetamide |
4-methylvaleroyl chloride
N-butyldeoxynojirimycin
1,5-(Butylimino)-1,5-dideoxy-D-glucitol, tetra(4-methylpentanoate)
Conditions | Yield |
---|---|
In tetrahydrofuran; pyridine; water; ethyl acetate |
1,2-dimethoxy-3-methylbenzene
p-toluenesulfonic acid monohydrate
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
In N-methyl-acetamide | |
In N-methyl-acetamide | |
In N-methyl-acetamide |
4,4,4-trifluorobutanoyl chloride
N-butyldeoxynojirimycin
Conditions | Yield |
---|---|
In tetrahydrofuran; pyridine; water |
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