• Name

  Diacetonefructose chlorosulfate

• EINECS
• CAS No. 150609-95-3
• Article Data11
• CAS DataBase
• Density 1.371 g/cm³
• Solubility
• Melting Point
• Formula C₁₂H₁₉ClO₈S
• Boiling Point 406.3 °C at 760 mmHg
• Molecular Weight 358.797
• Flash Point 199.5 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms b-D-Fructopyranose,2,3:4,5-bis-O-(1-methylethylidene)-, chlorosulfate (9CI);2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfonyl chloride;
• PSA 97.90000
• LogP 1.96550

Synthetic route

20880-92-6

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

Conditions

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%

7660-25-5

D-fructose

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

Conditions

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

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

97240-79-4

topiramate

Conditions

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%

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

20880-92-6

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

Conditions

Conditions	Yield
With ammonia In dichloromethane at 20 - 30℃; Temperature; Solvent;	90.7%

100-46-9

benzylamine

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

N-benzyl topiramate

Conditions

Conditions	Yield
In tetrahydrofuran at 23℃; for 24h;	76%

109-73-9

N-butylamine

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

Butyl-sulfamic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester

Conditions

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	67%

75-04-7

ethylamine

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

N-ethyl topiramate

Conditions

Conditions	Yield
In tetrahydrofuran 1.) -78 deg C, 60 min, 2.) 23 deg C, 2 h;	59%

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

106881-35-0

2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate

Conditions

Conditions	Yield
With pyridine; sodium azide In acetonitrile at 25 - 30℃; for 14h;

107-11-9

1-amino-2-propene

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

N-allyl-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20 - 50℃; for 4.16667h;

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

N-hydroxy-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In tetrahydrofuran; water at 20℃; for 12.17h;

236406-15-8

(4-methyl-piperidin-4-yl)-carbamic acid benzyl ester

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

1187321-63-6

C26H38N2O10S

Conditions

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;

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

1187321-64-7

C18H32N2O8S

Conditions

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

150609-95-3

2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

1187320-28-0

C25H40N4O9S

Conditions

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

Diacetonefructose chlorosulfate Specification