Product Name

  • Name

    SWAINSONINE

  • EINECS
  • CAS No. 72741-87-8
  • Article Data55
  • CAS DataBase
  • Density 1.382 g/cm3
  • Solubility
  • Melting Point 148-149oC
  • Formula C8H15NO3
  • Boiling Point 353.302 °C at 760 mmHg
  • Molecular Weight 173.212
  • Flash Point 209.735 °C
  • Transport Information
  • Appearance White Crystalline Solid
  • Safety 36
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 72741-87-8 (SWAINSONINE)
  • Hazard Symbols HarmfulXn
  • Synonyms 1,2,8-Indolizinetriol,octahydro-, [1S-(1a,2a,8b,8ab)]-;(-)-Swainsonine;D-Swainsonine;Swainsonine;Tridolgosir;(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol;(1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol;1,2,8-Indolizinetriol, octahydro-, (1S,2R,8R,8aR)-;
  • PSA 63.93000
  • LogP -1.51500

Synthetic route

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
72741-89-0

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
85624-09-5

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 12h; Ambient temperature;96%
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h;96%
With hydrogenchloride95%
(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine
129421-04-1

(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With hydrogenchloride at 65 - 70℃; for 0.5h;95%
(1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine
130412-86-1

(1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With hydrogen; palladium dichloride In methanol at 20℃; under 760 Torr; for 2h;93%
C14H27NO4Si

C14H27NO4Si

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
253778-10-8

[1S,2R,8R,8aR]-8-Triisopropylsilyloxy-1,2-(isopropylidenedioxy)indolizidine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
1002754-00-8

3-((2R,3S,4S,5S,6S)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
162470-36-2

(-)-8-benzyloxy-swainsonine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-styrylpiperidine

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-styrylpiperidine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
94349-19-6

(1S,2R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-octahydro-indolizine-1,2-diol

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
1148122-99-9

(3aR,9R,9aS,9bS)-9-(tert-butyldimethylsilyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 12h;83%
swainsonine tribenzylate
90706-28-8

swainsonine tribenzylate

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With cyclohexene; palladium dihydroxide72%
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
117270-04-9

(1S)-(1α,2α,8β,8aβ)-1-acetoxy-2,8-bis<(2,2-dimethylpropanoyl)oxy>octahydroindolizine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With methylamine In methanol for 46h;63%
(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)-1,2,3,5,8,8a-hexahydroindolizine
1579996-95-4

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)-1,2,3,5,8,8a-hexahydroindolizine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
132430-77-4

(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
124-63-0

methanesulfonyl chloride

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
113626-62-3

(2R,3S,4R)-N-benzyl-2-<(1R)-1-benzyloxy-4-hydroxybutanyl>-3,4-bis(benzyloxy)pyrrolidine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
107080-62-6, 127420-72-8, 98362-03-9

(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
92735-17-6

(3aS,4S,5aR,9aR,9bS)-4-Methoxy-2,2-dimethyl-octahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]pyridine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
107794-67-2

Benzoic acid (3aR,9R,9aR,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With sodium methylate; trifluoroacetic acid 1.) MeOH, r.t., 2.) H2O, r.t.; Yield given. Multistep reaction;
(3aR,9R,9aR,9bS)-5-Benzyl-9-benzyloxy-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-5-ium; chloride

(3aR,9R,9aR,9bS)-5-Benzyl-9-benzyloxy-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-5-ium; chloride

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
Yield given. Multistep reaction;
(1S,2R,8R,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride
113626-63-4

(1S,2R,8R,8aR)-4-Benzyl-1,2,8-tris-benzyloxy-octahydro-indolizinium; chloride

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol Yield given;
swainsonine diacetate
72741-88-9

swainsonine diacetate

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
154815-12-0

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
262282-77-9

(8R,8aR)-Octahydro-indolizine-1,2,8-triol

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
914616-18-5

(1R,8R,8aS)-8-(triisopropylsilyloxy)-octahydroindolizin-1-ol

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
262282-76-8

(8R,8aS)-8-Triisopropylsilanyloxy-octahydro-indolizine-1,2-diol

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
914616-14-1

(1R,8R,8aS)-1-hydroxy-8-(triisopropylsilyloxy)-tetrahydroindolizin-3(1H,2H,5H)-one

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
5-(1-hydroxyallyl)-4-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)pyrrolidin-2-one

5-(1-hydroxyallyl)-4-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)pyrrolidin-2-one

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
4-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)-5-((R)-1-(triisopropylsilyloxy)-allyl)-pyrrolidin-2-one

4-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)-5-((R)-1-(triisopropylsilyloxy)-allyl)-pyrrolidin-2-one

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
914616-13-0

(1R,8R,8aS)-1-((S)-1-(2,4,6-triisopropylphenyl)ethoxy)-8-(triisopropylsilyloxy)-8,8a-dihydroindolizin-3(1H,2H,5H)-one

swainsonine
72741-87-8

swainsonine

Conditions
ConditionsYield
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
72741-87-8

swainsonine

swainsonine N-oxide

swainsonine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol at 20 - 60℃; for 20h; Sealed tube;98%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

swainsonine
72741-87-8

swainsonine

1,2,8-tri-O-butyrylswainsonine

1,2,8-tri-O-butyrylswainsonine

Conditions
ConditionsYield
In pyridine at 25℃; for 48h;92%
swainsonine
72741-87-8

swainsonine

aspirin
50-78-2

aspirin

C17H21NO6

C17H21NO6

Conditions
ConditionsYield
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
72741-87-8

swainsonine

1195

1195

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol
85624-09-5

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 5℃; for 48h;85%
acetic anhydride
108-24-7

acetic anhydride

swainsonine
72741-87-8

swainsonine

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
72741-89-0

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester

Conditions
ConditionsYield
In pyridine at 25℃; for 48h;84%
swainsonine
72741-87-8

swainsonine

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol
85624-09-5

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1.25h; Heating;70%
2,2,2-trichloroethyl butyrate
57392-44-6

2,2,2-trichloroethyl butyrate

swainsonine
72741-87-8

swainsonine

A

2-O-butyrylswainsonine

2-O-butyrylswainsonine

B

1,2-di-O-butyrylswainsonine

1,2-di-O-butyrylswainsonine

Conditions
ConditionsYield
With porcine pancreatic lipase In tetrahydrofuran at 37℃; for 16h;A 6%
B 31%
2,2,2-trichloroethyl butyrate
57392-44-6

2,2,2-trichloroethyl butyrate

swainsonine
72741-87-8

swainsonine

2-O-butyrylswainsonine

2-O-butyrylswainsonine

Conditions
ConditionsYield
With subtilisin In pyridine at 45℃; for 72h;25%
swainsonine
72741-87-8

swainsonine

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester
72741-89-0

Acetic acid (1S,2R,8R,8aR)-1,2-diacetoxyoctahydroindolizin-8-yl ester

1,2,8-Indolizinetriol,octahydro-, (1S,2R,8R,8aR)- Specification

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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