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Miglustat
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Name

Miglustat

 EINECS N/A
CAS No. 72599-27-0 Density 1.2±0.1 g/cm3
PSA 84.16000 LogP -1.51640
Solubility Soluble in water at 10mg/ml Melting Point 126-127℃
Formula C10H21NO4 Boiling Point 394.7±42.0 °C at 760 mmHg
Molecular Weight 219.281 Flash Point 215.4±26.5 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 72599-27-0 (N-BUTYLDEOXYNOJIRIMYCIN) Hazard Symbols N/A
Synonyms

3,4,5-Piperidinetriol,1-butyl-2-(hydroxymethyl)-, [2R-(2a,3b,4a,5b)]-;Miglustat;N-Butyl-1-deoxynojirimycin;N-Butyldeoxynojirimycin;N-Butylmoranoline;NB-DNJ;OGT 918;SC 48334;Zavesca;

Article Data 31

Miglustat Synthetic route

210110-90-0

miglustat hydrochloride

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene99.5%
227932-82-3

N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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
109-65-9

1-bromo-butane

19130-96-2

1,5-dideoxy-1,5-imino-D-glucitol

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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;
19130-96-2

1,5-dideoxy-1,5-imino-D-glucitol

123-72-8

butyraldehyde

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; under 2585.81 Torr;60%
palladium In methanol
palladium In methanol
19684-22-1

D-xylo-hexos-5-ulose

109-73-9

N-butylamine

A

72599-27-0

N-butyldeoxynojirimycin

B

(3R,4R,5S)-6-Butylamino-hexane-1,2,3,4,5-pentaol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol 1.) -78 deg C, 2 h, 2.) r.t., 20 h;A 55%
B 10%

C24H33NO4

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
Stage #1: C24H33NO4 With trimethylsilyl iodide In dichloromethane at 20℃; for 0.25h;
Stage #2: With methanol In dichloromethane		33%
6564-72-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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
78136-16-0, 14233-48-8

2,3,4,6-tetra-O-benzyl-D-glucitol

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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
214041-43-7

(2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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
19684-32-3

1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose

72599-27-0

N-butyldeoxynojirimycin

Conditions
ConditionsYield
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

Miglustat Specification

The Miglustat, with the CAS registry number 72599-27-0, is also known as N-Butyl-1-deoxynojirimycin. This chemical's molecular formula is C10H21NO4 and molecular weight is 219.28. What's more, its systematic name is (2R,3R,4R,5S)-1-Butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol. Its classification codes are: (1)Anti-HIV agents; (2)Anti-Infective Agents; (3)Anti-Retroviral Agents; (4)Antiviral Agents; (5)Enzyme inhibitors; (6)Treatment of glycolipid storage diseases. This chemical is a glucosylceramide synthase inhibitor. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of Miglustat are: (1)ACD/LogP: 0.46±0.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.06; (4)ACD/LogD (pH 7.4): 0.31; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.27; (8)ACD/KOC (pH 7.4): 29.98; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 84.16 Å2; (13)Index of Refraction: 1.546; (14)Molar Refractivity: 56.2±0.3 cm3; (15)Molar Volume: 177.6±3.0 cm3; (16)Polarizability: 22.3±0.5×10-24cm3; (17)Surface Tension: 56.6±3.0 dyne/cm; (18)Density: 1.2±0.1 g/cm3; (19)Flash Point: 215.4±26.5 °C; (20)Enthalpy of Vaporization: 74.5±6.0 kJ/mol; (21)Boiling Point: 394.7±42.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±2.1 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CCCCN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
(2)Std. InChI: InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m1/s1
(3)Std. InChIKey: UQRORFVVSGFNRO-UTINFBMNSA-N

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