CAS No.72741-87-8,SWAINSONINE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	72741-87-8
Name:	SWAINSONINE
Article Data:	55

Formula:	C₈H₁₅NO₃
Molecular Weight:	173.212
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)-;
Density:	1.382 g/cm³
Melting Point:	148-149oC
Boiling Point:	353.302 °C at 760 mmHg
Flash Point:	209.735 °C
Appearance:	White Crystalline Solid
Hazard Symbols:	Xn
Risk Codes:	20/21/22
Safety:	36
PSA:	63.93000
LogP:	-1.51500

Synthetic route

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

: 72741-87-8
swainsonine

Conditions

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%

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

: 72741-87-8
swainsonine

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 12h; Ambient temperature;	96%
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h;	96%
With hydrogenchloride	95%

: 129421-04-1
(1S,2R,8R,8aR)-1,2-(cyclohexylidenedioxy)-8-hydroxyindolizidine

: 72741-87-8
swainsonine

Conditions

Conditions	Yield
With hydrogenchloride at 65 - 70℃; for 0.5h;	95%

: 130412-86-1
(1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine

: 72741-87-8
swainsonine

Conditions

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

: C14H27NO4Si

: 72741-87-8
swainsonine

Conditions

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%

: 253778-10-8
[1S,2R,8R,8aR]-8-Triisopropylsilyloxy-1,2-(isopropylidenedioxy)indolizidine

: 72741-87-8
swainsonine

Conditions

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 14h; Hydrolysis;	88%

: 1002754-00-8
3-((2R,3S,4S,5S,6S)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

: 72741-87-8
swainsonine

Conditions

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;

: 162470-36-2
(-)-8-benzyloxy-swainsonine

: 72741-87-8
swainsonine

Conditions

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

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

: 72741-87-8
swainsonine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h;	85%

: 94349-19-6
(1S,2R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-octahydro-indolizine-1,2-diol

: 72741-87-8
swainsonine

Conditions

Conditions	Yield
With Dowex 50W-X8 In methanol for 24h;	84%

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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