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-ARABINOSIDEInfo
- 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
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- 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-α-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)
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 |
Family
ID=27149270
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 |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT345480B (en) |
-
1975
- 1975-11-25 AT AT895175A patent/AT345480B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| ATA895175A (en) | 1978-01-15 |
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