AT345480B - PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE - Google Patents

PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE

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Publication number
AT345480B
AT345480B AT895175A AT895175A AT345480B AT 345480 B AT345480 B AT 345480B AT 895175 A AT895175 A AT 895175A AT 895175 A AT895175 A AT 895175A AT 345480 B AT345480 B AT 345480B
Authority
AT
Austria
Prior art keywords
arabinoside
digitoxigenin
preparation
new derivatives
alfa
Prior art date
Application number
AT895175A
Other languages
German (de)
Other versions
ATA895175A (en
Original Assignee
Boehringer Mannheim Gmbh
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
Priority claimed from DE2319874A external-priority patent/DE2319874C2/en
Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh
Priority to AT895175A priority Critical patent/AT345480B/en
Publication of ATA895175A publication Critical patent/ATA895175A/en
Application granted granted Critical
Publication of AT345480B publication Critical patent/AT345480B/en

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  • Saccharide Compounds (AREA)

Description

  

   <Desc/Clms Page number 1> 
 



   Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Derivaten des   Digitoxigenin-a-L-arabi-   nosids der allgemeinen Formel 
 EMI1.1 
 
 EMI1.2 
 

 <Desc/Clms Page number 2> 

 ; R,thylsulfat in 1, 6 ml Toluol zu. 30 min nach der letzten Zugabe wird mit 300 ml Chloroform verdünnt, über Kieselgur filtriert und mit Chloroform nachgewaschen. Zum Gesamtfiltrat gibt man 18 ml Pyridin, engt im 
 EMI2.1 
 aus, trocknet über Natriumsulfat und bringt die Chloroform-Äthanol-Phase zur Trockne. Das Rohprodukt enthält neben Monomethyläther verschiedene Dimethyläther und wird zur Reinigung, in Benzol-Chloroform   (l : l)   gelöst, über 20 g Aluminiumoxyd fraktioniert.

   Die Fraktionen mit 65 bis 70% Chloroform liefern nach Einengen und Kristallisation aus Chloroform-Äther 390 mg   3'-O-Methyldigitoxigenin-&alpha;-arabinosid.   



   Fp. = 186 bis   1900C.   hRF : 19.



   <Desc / Clms Page number 1>
 



   The invention relates to a process for the preparation of new derivatives of digitoxigenin-a-L-arabinoside of the general formula
 EMI1.1
 
 EMI1.2
 

 <Desc / Clms Page number 2>

 ; R, methyl sulfate in 1.6 ml of toluene. 30 minutes after the last addition, it is diluted with 300 ml of chloroform, filtered through kieselguhr and washed with chloroform. To the total filtrate is added 18 ml of pyridine, concentrated in
 EMI2.1
 out, dried over sodium sulfate and brought the chloroform-ethanol phase to dryness. In addition to monomethyl ether, the crude product contains various dimethyl ethers and is dissolved in benzene-chloroform (l: l) for purification and fractionated over 20 g of aluminum oxide.

   The fractions with 65 to 70% chloroform give, after concentration and crystallization from chloroform-ether, 390 mg of 3'-O-methyldigitoxigenin-α-arabinoside.



   Mp = 186 to 1900C. hRF: 19.

Claims (1)

PATENTANSPRUCH : Verfahren zur Herstellung von neuen Derivaten des Digitoxigenin-a-L-arabinosids der allgemeinen Formel EMI2.2 worin R,RundR gleich oder verschieden sind und je eine Alkylgruppe mit 1 bis 3 C-Atomen bedeuten, wobei auch einer oder zwei dieser Reste Wasserstoff sein kann, dadurch gekennzeichnet, dass man Digitoxigenin-&alpha;-L-arabinosid mit einem 0-Alkylierungsmittel umsetzt. PATENT CLAIM: Process for the preparation of new derivatives of digitoxigenin-a-L-arabinoside of the general formula EMI2.2 where R, RundR are identical or different and each represent an alkyl group with 1 to 3 carbon atoms, one or two of these radicals can also be hydrogen, characterized in that digitoxigenin-α-L-arabinoside is treated with an O-alkylating agent implements.
AT895175A 1973-04-19 1975-11-25 PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE AT345480B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT895175A AT345480B (en) 1973-04-19 1975-11-25 PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE2319874A DE2319874C2 (en) 1973-04-19 1973-04-19 Novel derivatives of digitoxigenin-α-L-arabinoside, processes for their preparation and medicaments containing them
AT321174A AT334550B (en) 1973-04-19 1974-04-18 PROCESS FOR THE PRODUCTION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALPHA-L -ARABINOSID
AT895175A AT345480B (en) 1973-04-19 1975-11-25 PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE

Publications (2)

Publication Number Publication Date
ATA895175A ATA895175A (en) 1978-01-15
AT345480B true AT345480B (en) 1978-09-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
AT895175A AT345480B (en) 1973-04-19 1975-11-25 PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF DIGITOXIGENIN-ALFA-L-ARABINOSIDE

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AT (1) AT345480B (en)

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Publication number Publication date
ATA895175A (en) 1978-01-15

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