CH235496A - Process for the production of a sugar derivative. - Google Patents
Process for the production of a sugar derivative.Info
- Publication number
- CH235496A CH235496A CH235496DA CH235496A CH 235496 A CH235496 A CH 235496A CH 235496D A CH235496D A CH 235496DA CH 235496 A CH235496 A CH 235496A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethyl
- reacted
- production
- sugar derivative
- diphenylethane
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
Verfahren zur Herstellung eines Zuckerderivates. Es wurde gefunden, dass man zu einem neuen Zuckerderivat gelangen kann, wenn man 4,4'-Dioxy-a,ss-diäthyl-diphenyläthan mit einem Mittel umsetzt, das tetraacylierte Glu- cosereste einzuführen vermag, und auf das so erhaltene Octaacyl-bis-glucosid verseifende Mittel einwirken lässt.
Mittel, die tetraäcy- lierte Glucosereste einzuführen vermögen, sind beispielsweise tetraacylierte Halogen- glucosen oder Pentaacylglucosen. Die Umset zung wird zweckmässig in Gegenwart von Lösungsmitteln und von Kondensationsmit teln vorgenommen.
Das so gewonnene 4,4'-Bis-(ss-glucosido)- a,ss-diäthyl-diphenyläthan bildet feine Na deln vom F. 2,66 bis 267 .
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel: 1 Teil 4,4'-Dioxy-a,ss-diäthyl-diphenyl- äthan, 3 Teile Pentaacetylglucose und 0,1 Teil Toluolsulfosäure werden in 10 Teilen Ben zol während 5 Stunden zum Sieden erhitzt.
Man wäscht hierauf die Lösung mit verdünn ter Natronlauge und Wasser und trocknet sie über Natriumsulfat. Nach Verdampfen des Benzols, zuletzt im Vakuum, gewinnt man das Octacetyl-bis-glucosid des Diogy-diäthyl- diphenyläthans in farblosen Kristallen. Es kann aus 96 7o Äthanol umgelöst werden und schmilzt rein bei 1$6 bis .188 .
Die Verseifung geschieht durch Erwär men der methanolischen Lösung des Acetyl- derivates mit 1 Teil einer Lösung von 1 Teil Natrium in 100 Teilen Methanol während kurzer Zeit. Man setzt Wasser zu, wobei das 4,4'-Bis - (,B- glucosido) <I>-</I> a,ss- diäthyl-diphenyl- äthan als weisses Pulver ausfällt.
Es bildet nach Umkristallisieren aus einem Methanol- Chloroform - Gemisch feine Nadeln vom F. 266 bis 267 .
An Stelle der Umsetzung mit Pentaacetyl- glucose in Gegenwart von p-Toluolsulfosäure kann auch mit Tetraacetobromglucöse in trockenem Chinolin unter Zusatz von Silber oxyd gearbeitet werden.
Process for the production of a sugar derivative. It has been found that a new sugar derivative can be obtained if 4,4'-dioxy-a, ss-diethyl-diphenylethane is reacted with an agent which is capable of introducing tetraacylated glucose residues and the octaacyl-bis obtained in this way -Lets glucoside saponifying agents act.
Agents which are able to introduce tetraacylated glucose residues are, for example, tetraacylated haloglucoses or pentaacylglucoses. The implementation is expediently carried out in the presence of solvents and condensation agents.
The 4,4'-bis (ss-glucosido) - a, ss-diethyl-diphenylethane obtained in this way forms fine needles with a temperature of 2.66 to 267.
The new compound should find therapeutic use.
Example: 1 part of 4,4'-dioxy-a, ss-diethyl-diphenyl-ethane, 3 parts of pentaacetylglucose and 0.1 part of toluenesulfonic acid are heated to boiling in 10 parts of benzene for 5 hours.
The solution is then washed with dilute sodium hydroxide solution and water and dried over sodium sulfate. After evaporation of the benzene, finally in vacuo, the octacetyl-bis-glucoside of diogy-diethyl-diphenylethane is obtained in colorless crystals. It can be redissolved from 96 7o ethanol and melts at 1 $ 6 to .188.
The saponification is done by heating the methanolic solution of the acetyl derivative with 1 part of a solution of 1 part of sodium in 100 parts of methanol for a short time. Water is added, the 4,4'-bis (, B-glucosido) α, ß-diethyl-diphenyl-ethane precipitating as a white powder.
After recrystallization from a methanol-chloroform mixture, it forms fine needles with a mp of 266 to 267.
Instead of the reaction with pentaacetylglucose in the presence of p-toluenesulfonic acid, tetraacetobromoglucose in dry quinoline with the addition of silver oxide can also be used.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH229075T | 1938-03-16 | ||
CH235496T | 1938-03-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH235496A true CH235496A (en) | 1944-11-30 |
Family
ID=25727297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH235496D CH235496A (en) | 1938-03-16 | 1938-03-16 | Process for the production of a sugar derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH235496A (en) |
-
1938
- 1938-03-16 CH CH235496D patent/CH235496A/en unknown
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