Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
swainsonine
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; Hydrolysis; | 100% |
With Amberlite IRA-402 In methanol for 18h; | 97% |
With Amberlite IRA-401(OH) In methanol at 20℃; for 2h; | 96% |
(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran for 12h; Ambient temperature; | 96% |
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h; | 96% |
With hydrogenchloride | 95% |
(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride at 65 - 70℃; for 0.5h; | 95% |
(1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine
swainsonine
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In methanol at 20℃; under 760 Torr; for 2h; | 93% |
swainsonine
Conditions | Yield |
---|---|
Stage #1: C14H27NO4Si With hydrogenchloride In methanol at 20℃; for 3h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 8h; Reflux; | 90% |
[1S,2R,8R,8aR]-8-Triisopropylsilyloxy-1,2-(isopropylidenedioxy)indolizidine
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 14h; Hydrolysis; | 88% |
3-((2R,3S,4S,5S,6S)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate
swainsonine
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In ethanol at 20℃; under 5171.62 Torr; for 72h; | 86% |
With hydrogen; palladium dihydroxide In ethanol at 20℃; under 5171.48 Torr; |
(-)-8-benzyloxy-swainsonine
swainsonine
Conditions | Yield |
---|---|
Stage #1: (-)-8-benzyloxy-swainsonine With hydrogen; palladium dichloride In methanol at 20℃; under 760.051 Torr; for 1h; Stage #2: In water | 85% |
Multi-step reaction with 3 steps 1: 60 mg / p-toluenesulfonic acid / CH2Cl2 / 3 h / 20 °C 2: 100 percent / H2; palladium(II) chloride / methanol / 0.5 h / 20 °C 3: 94.3 percent / hydrochloric acid / H2O; tetrahydrofuran / 20 h / 20 °C View Scheme |
swainsonine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h; | 85% |
(1S,2R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-octahydro-indolizine-1,2-diol
swainsonine
Conditions | Yield |
---|---|
With Dowex 50W-X8 In methanol for 24h; | 84% |
(3aR,9R,9aS,9bS)-9-(tert-butyldimethylsilyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizine
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 12h; | 83% |
swainsonine tribenzylate
swainsonine
Conditions | Yield |
---|---|
With cyclohexene; palladium dihydroxide | 72% |
With cyclohexene; palladium dihydroxide In ethanol for 44h; Heating; | 72% |
(1S)-(1α,2α,8β,8aβ)-1-acetoxy-2,8-bis<(2,2-dimethylpropanoyl)oxy>octahydroindolizine
swainsonine
Conditions | Yield |
---|---|
With methylamine In methanol for 46h; | 63% |
(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)-1,2,3,5,8,8a-hexahydroindolizine
swainsonine
Conditions | Yield |
---|---|
Stage #1: (1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)-1,2,3,5,8,8a-hexahydroindolizine With hydrogenchloride; 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; water at 20℃; under 760.051 Torr; for 48h; Inert atmosphere; Stage #2: In methanol; water | 62% |
(R)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol
methanesulfonyl chloride
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h; Yield given. Multistep reaction; |
(2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-4-hydroxybutanyl>-3,4-bis(benzyloxy)pyrrolidine
methanesulfonyl chloride
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h; Yield given. Multistep reaction; |
(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one
swainsonine
Conditions | Yield |
---|---|
With dimethylsulfide; borane; trifluoroacetic acid Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: 94 percent / borane-methyl sulfide complex / tetrahydrofuran / 0 deg C, 30 min, room temperature, 2 h 2: 96 percent / conc. HCl / tetrahydrofuran / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 60 percent / NaBH4 / ethanol; tetrahydrofuran / Heating 2: 75 percent / 6N HCl / tetrahydrofuran / Ambient temperature View Scheme |
(3aS,4S,5aR,9aR,9bS)-4-Methoxy-2,2-dimethyl-octahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]pyridine
swainsonine
Conditions | Yield |
---|---|
With boron trichloride; sodium cyanoborohydride 1.) -78 deg C, 1.5 h, CHCl3; RT, 16 h, CHCl3, 2.) MeOH/H2O(1:1), pH=(6-7) (with 0.1 mol/l hydrochloric acid), RT, 24 h; Yield given. Multistep reaction; |
Benzoic acid (3aR,9R,9aR,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester
swainsonine
Conditions | Yield |
---|---|
With sodium methylate; trifluoroacetic acid 1.) MeOH, r.t., 2.) H2O, r.t.; Yield given. Multistep reaction; |
swainsonine
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
(1S,2R,8R,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol Yield given; |
swainsonine diacetate
swainsonine
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 25℃; for 24h; | 10 mg |
(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine
swainsonine
Conditions | Yield |
---|---|
Stage #1: (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine With hydrogen; palladium dichloride Stage #2: With hydrogenchloride | |
Multi-step reaction with 2 steps 1: 100 percent / H2; palladium(II) chloride / methanol / 0.5 h / 20 °C 2: 94.3 percent / hydrochloric acid / H2O; tetrahydrofuran / 20 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: HCOOH / Pd/C / methanol / 2 h 2: 39 mg / 6N HCl / tetrahydrofuran / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 86 percent / H2 / PdCl2 / methanol / 0.5 h 2: 66 percent / 2 N aq. HCl / tetrahydrofuran / 14 h / Ambient temperature View Scheme |
(8R,8aR)-Octahydro-indolizine-1,2,8-triol
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 2: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
(1R,8R,8aS)-8-(triisopropylsilyloxy)-octahydroindolizin-1-ol
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: Martin sulfurane / diethyl ether / 0.5 h / 0 °C 2: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 216 h / 4 °C 3: TBAF / tetrahydrofuran / 27 h / 20 °C 4: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 5: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
(8R,8aS)-8-Triisopropylsilanyloxy-octahydro-indolizine-1,2-diol
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: TBAF / tetrahydrofuran / 27 h / 20 °C 2: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 3: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
(1R,8R,8aS)-1-hydroxy-8-(triisopropylsilyloxy)-tetrahydroindolizin-3(1H,2H,5H)-one
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: LiAlH4 / tetrahydrofuran / 1.3 h / Heating 1.2: 92 percent / aq.NaOH; water / 20 °C 2.1: Martin sulfurane / diethyl ether / 0.5 h / 0 °C 3.1: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 216 h / 4 °C 4.1: TBAF / tetrahydrofuran / 27 h / 20 °C 5.1: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 6.1: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: i-Pr2NEt / CH2Cl2 / 1 h 1.2: 81 percent / AcOH / tetrahydrofuran; H2O 2.1: 95 percent / n-Bu4N; H2SO4 / CH2Cl2; aq. NaOH / 20 °C 3.1: 84 percent / Grubbs II catalyst / CH2Cl2 / 3 h / Heating 4.1: 87 percent / H2 / Pd/C / ethyl acetate / 2.5 h / 20 °C 5.1: 97 percent / TFA / CH2Cl2 / 20 °C 6.1: LiAlH4 / tetrahydrofuran / 1.3 h / Heating 6.2: 92 percent / aq.NaOH; water / 20 °C 7.1: Martin sulfurane / diethyl ether / 0.5 h / 0 °C 8.1: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 216 h / 4 °C 9.1: TBAF / tetrahydrofuran / 27 h / 20 °C 10.1: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 11.1: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 95 percent / n-Bu4N; H2SO4 / CH2Cl2; aq. NaOH / 20 °C 2.1: 84 percent / Grubbs II catalyst / CH2Cl2 / 3 h / Heating 3.1: 87 percent / H2 / Pd/C / ethyl acetate / 2.5 h / 20 °C 4.1: 97 percent / TFA / CH2Cl2 / 20 °C 5.1: LiAlH4 / tetrahydrofuran / 1.3 h / Heating 5.2: 92 percent / aq.NaOH; water / 20 °C 6.1: Martin sulfurane / diethyl ether / 0.5 h / 0 °C 7.1: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 216 h / 4 °C 8.1: TBAF / tetrahydrofuran / 27 h / 20 °C 9.1: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 10.1: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
(1R,8R,8aS)-1-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)-8-(triisopropylsilyloxy)-8,8a-dihydroindolizin-3(1H,2H,5H)-one
swainsonine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 87 percent / H2 / Pd/C / ethyl acetate / 2.5 h / 20 °C 2.1: 97 percent / TFA / CH2Cl2 / 20 °C 3.1: LiAlH4 / tetrahydrofuran / 1.3 h / Heating 3.2: 92 percent / aq.NaOH; water / 20 °C 4.1: Martin sulfurane / diethyl ether / 0.5 h / 0 °C 5.1: AD-mix-α; methylsulfonamide / 2-methyl-propan-2-ol; H2O / 216 h / 4 °C 6.1: TBAF / tetrahydrofuran / 27 h / 20 °C 7.1: 143 mg / DMAP / CH2Cl2; pyridine / 48 h 8.1: 97 percent / amberlite IRA-402 / methanol / 18 h View Scheme |
swainsonine
Conditions | Yield |
---|---|
With dihydrogen peroxide In ethanol at 20 - 60℃; for 20h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
In pyridine at 25℃; for 48h; | 92% |
Conditions | Yield |
---|---|
Stage #1: aspirin With thionyl chloride; N,N-dimethyl-formamide at 25℃; for 1h; Cooling with ice; Stage #2: swainsonine at 25℃; for 10h; Time; | 88.2% |
swainsonine
(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone at 5℃; for 48h; | 85% |
acetic anhydride
swainsonine
Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
Conditions | Yield |
---|---|
In pyridine at 25℃; for 48h; | 84% |
swainsonine
2,2-dimethoxy-propane
(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 1.25h; Heating; | 70% |
2,2,2-trichloroethyl butyrate
swainsonine
Conditions | Yield |
---|---|
With porcine pancreatic lipase In tetrahydrofuran at 37℃; for 16h; | A 6% B 31% |
Conditions | Yield |
---|---|
With subtilisin In pyridine at 45℃; for 72h; | 25% |
swainsonine
Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
The 1,2,8-Indolizinetriol,octahydro-, (1S,2R,8R,8aR)-, with the CAS registry number 72741-87-8, has the systematic name of (1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol. It is a kind of white crystalline solid, and belongs to the following product categories: Alkaloids; Glycosidase Inhibitors; Inhibitors. And the molecular formula of the chemical is C8H15NO3.
The characteristics of 1,2,8-Indolizinetriol,octahydro-, (1S,2R,8R,8aR)- are as followings: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 6.568; (7)#H bond acceptors: 4; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 63.93 Å2; (11)Index of Refraction: 1.609; (12)Molar Refractivity: 43.396 cm3; (13)Molar Volume: 125.351 cm3; (14)Polarizability: 17.204×10-24cm3; (15)Surface Tension: 68.456 dyne/cm; (16)Density: 1.382 g/cm3; (17)Flash Point: 209.735 °C; (18)Enthalpy of Vaporization: 69.263 kJ/mol; (19)Boiling Point: 353.302 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Uses of 1,2,8-Indolizinetriol,octahydro-, (1S,2R,8R,8aR)-: It is a plant alkaloid derived from Swainsona canescens (a leguminous plant). And it is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydroly.
You should be cautious while dealing with this chemical. It is harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better wear suitable protective clothing.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
(2)InChI: InChI=1/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
(3)InChIKey: FXUAIOOAOAVCGD-WCTZXXKLBP
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