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
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH235496A publication Critical patent/CH235496A/en

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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

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  • 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)

PATENTANSPRUCH: Verfahren zur Herstellung eines Zucker derivates, dadurch gekennzeichnet, dass man 4,4'- Diogy - a,ss <I>-</I> diäthyl - diphenyläthan mit einem Mittel umsetzt, das tetraacylierte Glu- cosereste einzuführen vermag und auf das erhaltene Octaacyl-bis-glucosid verseifende Mittel einwirken lässt. Das so gewonnene 4,4'-ssis-(ss-glucosido)- a,ss-diäthyl-diphenyläthan bildet feine Nadeln vom F. 266 bis 267 . Die neue Verbindung soll therapeutische Verwendung finden. PATENT CLAIM: A process for the production of a sugar derivative, characterized in that 4,4'-Diogy - a, ss <I> - </I> diethyl - diphenylethane is reacted with an agent which is able to introduce the tetraacylated glucose residues and to which Octaacyl-bis-glucoside saponifying agents obtained can act. The 4,4'-ssis- (ss-glucosido) - a, ss-diethyl-diphenylethane obtained in this way forms fine needles with a diameter of 266 to 267. The new compound should find therapeutic use. LTN TER AN SPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man mit Penta- acetylglucose umsetzt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man mit Tetra- acetobromglucose umsetzt. LTN TER AN APPROACH 1. Process according to patent claim, characterized in that it is reacted with pentaacetylglucose. 2. The method according to claim, characterized in that it is reacted with tetraacetobromoglucose.
CH235496D 1938-03-16 1938-03-16 Process for the production of a sugar derivative. CH235496A (en)

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)

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