BE668116A - - Google Patents
Info
- Publication number
- BE668116A BE668116A BE668116DA BE668116A BE 668116 A BE668116 A BE 668116A BE 668116D A BE668116D A BE 668116DA BE 668116 A BE668116 A BE 668116A
- Authority
- BE
- Belgium
- Prior art keywords
- acetic anhydride
- acetyl
- glucosides
- boiling
- acetylated
- Prior art date
Links
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 36
- 229930182478 glucoside Natural products 0.000 claims description 11
- 150000008131 glucosides Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 230000021736 acetylation Effects 0.000 claims description 6
- 238000006640 acetylation reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 230000003177 cardiotonic effect Effects 0.000 claims description 4
- RXRFEELZASHOLV-JAJWTYFOSA-N [(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] acetate Chemical compound CC(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RXRFEELZASHOLV-JAJWTYFOSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OCEDEAQHBIGPTE-UHFFFAOYSA-N Gitoxin Natural products CC1OC(CC(O)C1O)OC2C(O)CC(OC3C(O)CC(OC4CCC5(C)C(CCC6C5CCC7(C)C(C(O)CC67O)C8=CCOC8=O)C4)OC3C)OC2C OCEDEAQHBIGPTE-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- LKRDZKPBAOKJBT-CNPIRKNPSA-N gitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(C[C@H](O)[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LKRDZKPBAOKJBT-CNPIRKNPSA-N 0.000 description 4
- 229950000974 gitoxin Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940097217 cardiac glycoside Drugs 0.000 description 3
- 239000002368 cardiac glycoside Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229930002534 steroid glycoside Natural products 0.000 description 3
- 150000008143 steroidal glycosides Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- JDYLJSDIEBHXPO-ALNZGLKXSA-N [(2r,3r,4s,6r)-3-[(2s,4s,5r,6r)-4-acetyloxy-5-[(2s,4s,5r,6r)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-[[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-16-acetyloxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17 Chemical compound O([C@H]1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)O[C@H]1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@H]([C@]4(C[C@@H]([C@@H]([C@@]4(C)CC3)C=3COC(=O)C=3)OC(C)=O)O)CC2)(C)CC1)[C@H]1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 JDYLJSDIEBHXPO-ALNZGLKXSA-N 0.000 description 2
- PUCLYQTTYFLJOQ-QWAIYLRASA-N [(2r,4s,6r)-3-[(2s,4s,5r,6r)-4-acetyloxy-5-[(2s,4s,5r,6r)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-[[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecah Chemical compound O([C@H]1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)OC1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@H]([C@]4(C[C@H](O)[C@@H]([C@@]4(C)CC3)C=3COC(=O)C=3)O)CC2)(C)CC1)[C@H]1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 PUCLYQTTYFLJOQ-QWAIYLRASA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HPMZBILYSWLILX-UMDUKNJSSA-N 3'''-O-acetyldigitoxin Chemical compound C1[C@H](OC(C)=O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O HPMZBILYSWLILX-UMDUKNJSSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XUTZHKBFRMSIQE-REFIZGJZSA-N [(2r,3r,4s,6s)-3-[(2r,4s,5r,6r)-4-acetyloxy-5-[(2r,4s,5r,6r)-4,5-diacetyloxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-[[(3s,5r,8r,9s,10s,13r,17r)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclop Chemical compound O([C@H]1[C@@H](OC(C)=O)C[C@H](O[C@@H]1C)O[C@H]1[C@@H](OC(C)=O)C[C@H](O[C@@H]1C)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@H](C4(CC[C@@H]([C@@]4(C)CC3)C=3COC(=O)C=3)O)CC2)(C)CC1)[C@@H]1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](C)O1 XUTZHKBFRMSIQE-REFIZGJZSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960000648 digitoxin Drugs 0.000 description 1
- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 gitoxin Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N methyl ethyl ketone Substances CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QEGHEEOQRPNAOD-UHFFFAOYSA-N pyridin-2-ylmethanol;hydrate Chemical compound O.OCC1=CC=CC=N1 QEGHEEOQRPNAOD-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6506250A NL6506250A (d) | 1965-05-17 | 1965-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE668116A true BE668116A (d) |
Family
ID=19793167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE668116D BE668116A (d) | 1965-05-17 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE668116A (d) |
| NL (1) | NL6506250A (d) |
-
0
- BE BE668116D patent/BE668116A/fr unknown
-
1965
- 1965-05-17 NL NL6506250A patent/NL6506250A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6506250A (d) | 1966-11-18 |
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