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Voglibose
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Name

Voglibose

 EINECS 1312995-182-4
CAS No. 83480-29-9 Density 1.58 g/cm3
PSA 153.64000 LogP -4.10150
Solubility N/A Melting Point 162-163 °C
Formula C10H21NO7 Boiling Point 601.9 °C at 760 mmHg
Molecular Weight 267.279 Flash Point 274.1 °C
Transport Information N/A Appearance Colourless crystalline solid
Safety 36/37-37/39-26 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 83480-29-9 (Voglibose) Hazard Symbols IrritantXi
Synonyms

Vioglibose;n-(1,3-dihydroxy-2-propyl)valiolamine;5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol;AO 128;Voglibose (JAN/USAN);Basen (TN);A 71100;3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epi-inositol;Basen;(1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol;Voglibosa [INN-Spanish];Voglibosum [INN-Latin];3,4-Dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol;D-epi-Inositol,3,4-dideoxy-4-[[2-hydroxy-1- (hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-;

Article Data 20

Voglibose Synthetic route

115250-39-0

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; palladium In methanol Ambient temperature;94%
With boron trifluoride diethyl etherate; diisopropylamine In tetrahydrofuran at 15 - 30℃; Reagent/catalyst; Solvent;82.86%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In tetrahydrofuran; methanol; water at 20℃; under 2206.72 - 2574.5 Torr; for 3h;
96-26-4

dihydroxyacetone

83465-22-9

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

83480-29-9

voglibose

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 24h;85%
With hydrogenchloride; water; sodium cyanoborohydride In water; N,N-dimethyl-formamide at 70℃; for 16h;82%
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 50 - 60℃; for 15h;73%
Stage #1: dihydroxyacetone; (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: With sodium cyanoborohydride In water; N,N-dimethyl-formamide at 20℃; for 16h;		3 g

C42H41NO13

83480-29-9

voglibose

Conditions
ConditionsYield
In water for 24h; Reflux;85%

C10H19NO7

83480-29-9

voglibose

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; N,N-dimethyl-formamide at 0 - 50℃; for 24h; Reagent/catalyst; Temperature;80%

3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-1,5,6-tris-O-(phenylmethyl)-D-epi-inositol

83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; water; palladium In methanol at 20 - 60℃; for 6h;65%
115250-38-9

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol

83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / NaBH3CN / methanol / 16 h / Ambient temperature
2: 94 percent / 90 percent formic acid, Pd-black / methanol / Ambient temperature
View Scheme
849419-34-7

voglibose hydrochloride

83480-29-9

voglibose

Conditions
ConditionsYield
With triethylamine In methanol for 1h; pH=~ 8.8 - ~ 9.0;
115250-39-0

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

A

4-benzyl-voglibose

B

83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; palladium on activated charcoal In methanol; water Inert atmosphere;A 0.7 g
B 16 g
38231-86-6

valienamine

83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 5 h / 0 - 20 °C
1.2: 48 h / 40 °C
1.3: 6 h / 0 - 20 °C
2.1: sodium tetrahydroborate / N,N-dimethyl-formamide; methanol / 24 h / 0 - 50 °C
3.1: hydrogenchloride; sodium cyanoborohydride / N,N-dimethyl-formamide / 24 h / 60 °C
View Scheme
82920-27-2

N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine

83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 3 h / 0 - 20 °C
1.2: 24 h / 40 °C
1.3: 3.5 h / 0 - 20 °C
2.1: sodium tetrahydroborate / N,N-dimethyl-formamide; methanol / 24 h / 0 - 50 °C
View Scheme

Voglibose Chemical Properties

The Molecular Structure of Voglibose (CAS NO.83480-29-9):

Empirical Formula: C10H21NO7
Molecular Weight: 267.2762
IUPAC Name: (1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol  
Appearance:  Colourless Crystalline Solid
Nominal Mass: 267 Da
Average Mass: 267.2762 Da
Monoisotopic Mass: 267.131802 Da 
Index of Refraction: 1.635
Molar Refractivity: 60.59 cm3
Molar Volume: 169.1 cm3
Surface Tension: 99.7 dyne/cm
Density: 1.58 g/cm3
Flash Point: 274.1 °C
Enthalpy of Vaporization: 102.74 kJ/mol
Boiling Point: 601.9 °C at 760 mmHg
Vapour Pressure: 5.37E-17 mmHg at 25°C 
InChI
InChI=1/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2
Smiles
C1[C@@](O)(CO)[C@@H]([C@@H]([C@@H](O)[C@@H]1NC(CO)CO)O)O 
Product Categories: Miscellaneous;VOGLIBOSE;All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals

Voglibose Uses

 Voglibose (CAS NO.83480-29-9) can be used in the treatment of diabetes.

Voglibose Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 2gm/kg (2000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
mouse LD50 intravenous 7820mg/kg (7820mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
mouse LD50 oral 14700mg/kg (14700mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
rat LD50 intravenous 6300mg/kg (6300mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.
rat LD50 oral 20gm/kg (20000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 25, Pg. 815, 1994.

Voglibose Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 20/21/22-36/37/38 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 36/37-37/39-26 
S36/37: Wear suitable protective clothing and gloves
S37/39: Wear suitable gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RTECS: NM7524600

Voglibose Specification

 Voglibose (CAS NO.83480-29-9) is also called as Voglibose [USAN:INN] ; 3,4-Dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol ; Voglibosa ; Voglibosa [INN-Spanish] ; Voglibose ; Voglibosum ; Voglibosum [INN-Latin] ; 3,4-Dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol .There are three molecules which belong to this class namely, Acarbose, Miglitol and Voglibose (CAS NO.83480-29-9). Voglibose (CAS NO.83480-29-9) is the latest molecule in this class. Voglibose (CAS NO.83480-29-9) scores over both Acarbose and MIglitol in terms of side effect profile. But Acarbose has an edge over Voglibose (CAS NO.83480-29-9) in terms of efficacy(FBG , PPBG , HBA1C).

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