2,3;4,5-di-O-isopropylidene-β-D-fructopyranose
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
With sulfuryl dichloride In dichloromethane; toluene at -5 - 20℃; for 6h; Temperature; Reagent/catalyst; Inert atmosphere; | 95.9% |
With pyridine; sulfuryl dichloride In 1,2-dichloro-ethane at -20 - 25℃; for 2 - 7h; Product distribution / selectivity; | 94% |
With pyridine; sulfuryl dichloride In dichloromethane; toluene at -10 - 20℃; for 3h; Temperature; | 93.7% |
D-fructose
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: zinc(II) chloride / 2 h / 58 °C 2: sulfuryl dichloride; 1H-imidazole / dichloromethane / 2.5 h / 0 °C / Molecular sieve View Scheme |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
topiramate
Conditions | Yield |
---|---|
With ammonia In tetrahydrofuran; hexane at 20℃; for 3h; Solvent; Temperature; | 96.7% |
With ammonia In tetrahydrofuran; Petroleum ether at 20℃; for 3h; Solvent; | 95.2% |
With pyridine; SULFAMIDE In 5,5-dimethyl-1,3-cyclohexadiene at 128 - 133℃; for 3h; | 91.1% |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose
Conditions | Yield |
---|---|
With ammonia In dichloromethane at 20 - 30℃; Temperature; Solvent; | 90.7% |
benzylamine
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 23℃; for 24h; | 76% |
N-butylamine
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; Heating; | 67% |
ethylamine
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
In tetrahydrofuran 1.) -78 deg C, 60 min, 2.) 23 deg C, 2 h; | 59% |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate
Conditions | Yield |
---|---|
With pyridine; sodium azide In acetonitrile at 25 - 30℃; for 14h; |
1-amino-2-propene
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20 - 50℃; for 4.16667h; |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; potassium carbonate In tetrahydrofuran; water at 20℃; for 12.17h; |
(4-methyl-piperidin-4-yl)-carbamic acid benzyl ester
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
C26H38N2O10S
Conditions | Yield |
---|---|
Stage #1: (4-methyl-piperidin-4-yl)-carbamic acid benzyl ester With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester In tetrahydrofuran at 20℃; for 1.25h; |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
C18H32N2O8S
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C 1.2: 1.25 h / 20 °C 2.1: hydrogen / 5%-palladium/activated carbon / ethanol / 0.33 h View Scheme |
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester
C25H40N4O9S
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C 1.2: 1.25 h / 20 °C 2.1: hydrogen / 5%-palladium/activated carbon / ethanol / 0.33 h 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 65 °C View Scheme |
The cas register number of Diacetonefructose chlorosulfate is 150609-95-3. It also can be called as 2,3:4,5-bis-O-(1-methylethylidene)-b-D-Fructopyranose and the Systematic name about this chemical is [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl chlorosulfate (non-preferred name). It belongs to the Pharmaceutical Intermediates.
Physical properties about Diacetonefructose chlorosulfate are: (1)ACD/LogP: 4.49; (2)ACD/LogD (pH 5.5): 4.49; (3)ACD/LogD (pH 7.4): 4.49; (4)ACD/BCF (pH 5.5): 1533.45; (5)ACD/BCF (pH 7.4): 1533.45; (6)ACD/KOC (pH 5.5): 6635.92; (7)ACD/KOC (pH 7.4): 6635.92; (8)#H bond acceptors: 8; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 97.9Å2; (11)Index of Refraction: 1.489; (12)Molar Refractivity: 75.53 cm3; (13)Molar Volume: 261.5 cm3; (14)Polarizability: 29.94x10-24cm3; (15)Surface Tension: 50 dyne/cm; (16)Enthalpy of Vaporization: 63.24 kJ/mol; (17)Boiling Point: 406.3 °C at 760 mmHg; (18)Vapour Pressure: 1.93E-06 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: ClS(=O)(=O)OC[C@@]21OC(O[C@H]1[C@@H]3OC(O[C@@H]3CO2)(C)C)(C)C
(2)InChI: InChI=1/C12H19ClO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3/t7-,8-,9+,12+/m1/s1
(3)InChIKey: RXVWCMYRBRBGMC-XBWDGYHZBG
(4)Std. InChI: InChI=1S/C12H19ClO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3/t7-,8-,9+,12+/m1/s1
(5)Std. InChIKey: RXVWCMYRBRBGMC-XBWDGYHZSA-N
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