GB1420879A - Pseudodi- and trisaccharides and methods for their preparation - Google Patents
Pseudodi- and trisaccharides and methods for their preparationInfo
- Publication number
- GB1420879A GB1420879A GB4643173A GB4643173A GB1420879A GB 1420879 A GB1420879 A GB 1420879A GB 4643173 A GB4643173 A GB 4643173A GB 4643173 A GB4643173 A GB 4643173A GB 1420879 A GB1420879 A GB 1420879A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydroxy
- protective
- amino
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000004043 trisaccharides Chemical class 0.000 title abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 9
- 125000005646 oximino group Chemical group 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 7
- -1 hydroxy, amino Chemical group 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 125000003282 alkyl amino group Chemical group 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 230000008030 elimination Effects 0.000 abstract 3
- 238000003379 elimination reaction Methods 0.000 abstract 3
- 125000000468 ketone group Chemical group 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 150000002772 monosaccharides Chemical class 0.000 abstract 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000908 ammonium hydroxide Substances 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 2
- 150000002917 oxazolidines Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 abstract 2
- DTFAJAKTSMLKAT-KFJBKXNJSA-N (1s,3r,4s,6r)-4,6-diaminocyclohexane-1,2,3-triol Chemical group N[C@H]1C[C@@H](N)[C@H](O)C(O)[C@@H]1O DTFAJAKTSMLKAT-KFJBKXNJSA-N 0.000 abstract 1
- XUFIWSHGXVLULG-BSBKYKEKSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-[(1s)-1-aminoethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUFIWSHGXVLULG-BSBKYKEKSA-N 0.000 abstract 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 abstract 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 abstract 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- ONKJLIUSEXIAKL-UHFFFAOYSA-N Garamine Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(O)C(N)CC1N ONKJLIUSEXIAKL-UHFFFAOYSA-N 0.000 abstract 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical class O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 229940053194 antiepileptics oxazolidine derivative Drugs 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- ONKJLIUSEXIAKL-QUDADGMASA-N garamine Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](N)C[C@H]1N ONKJLIUSEXIAKL-QUDADGMASA-N 0.000 abstract 1
- DNYGXMICFMACRA-UHFFFAOYSA-N gentamicin C1A Natural products O1C(CNC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N DNYGXMICFMACRA-UHFFFAOYSA-N 0.000 abstract 1
- XUFIWSHGXVLULG-JYDJLPLMSA-N gentamycin C2 Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)[C@@H](C)N)N)[C@@H](N)C[C@H]1N XUFIWSHGXVLULG-JYDJLPLMSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 229940040102 levulinic acid Drugs 0.000 abstract 1
- 229940075610 mercuric cyanide Drugs 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229910001958 silver carbonate Inorganic materials 0.000 abstract 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 abstract 1
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical class [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
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
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29643472A | 1972-10-10 | 1972-10-10 | |
| US30806172A | 1972-11-20 | 1972-11-20 | |
| US39191473A | 1973-08-27 | 1973-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1420879A true GB1420879A (en) | 1976-01-14 |
Family
ID=27404431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4643173A Expired GB1420879A (en) | 1972-10-10 | 1973-10-04 | Pseudodi- and trisaccharides and methods for their preparation |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS49100052A (enrdf_load_stackoverflow) |
| BG (1) | BG21607A3 (enrdf_load_stackoverflow) |
| DE (1) | DE2349974A1 (enrdf_load_stackoverflow) |
| ES (1) | ES419364A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2201872B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1420879A (enrdf_load_stackoverflow) |
| IL (1) | IL43368A0 (enrdf_load_stackoverflow) |
| NL (1) | NL7313668A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2860513D1 (en) * | 1977-06-24 | 1981-04-09 | Scherico Ltd | Process for preparing aminoglycoside derivatives, novel derivatives obtained and pharmaceutical compositions containing such derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH79A (de) * | 1889-01-09 | Adam Sautter Johann | Uhrwerk für Taschenuhren mit offenem Federhaus, neuem Gangrücker-System und vereinfachter Werkbefestigung | |
| CH551965A (de) * | 1970-06-22 | 1974-07-31 | Scherico Ltd | Verfahren zur herstellung antibiotisch wirksamer verbindungen. |
| BE787758A (fr) * | 1971-11-08 | 1973-02-19 | Scherico Ltd | Procede de preparation d'une substance douee d'activite antibiotique contenant un nouvel antibiotique, et de derives de celle-ci |
-
1973
- 1973-10-04 DE DE19732349974 patent/DE2349974A1/de active Pending
- 1973-10-04 FR FR7335539A patent/FR2201872B1/fr not_active Expired
- 1973-10-04 GB GB4643173A patent/GB1420879A/en not_active Expired
- 1973-10-04 IL IL43368A patent/IL43368A0/xx unknown
- 1973-10-04 NL NL7313668A patent/NL7313668A/xx unknown
- 1973-10-05 JP JP48111633A patent/JPS49100052A/ja active Pending
- 1973-10-05 ES ES419364A patent/ES419364A1/es not_active Expired
- 1973-10-09 BG BG024695A patent/BG21607A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2201872B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| BG21607A3 (bg) | 1976-07-20 |
| DE2349974A1 (de) | 1974-04-18 |
| FR2201872A1 (enrdf_load_stackoverflow) | 1974-05-03 |
| ES419364A1 (es) | 1976-07-16 |
| JPS49100052A (enrdf_load_stackoverflow) | 1974-09-20 |
| AU6107173A (en) | 1975-04-10 |
| IL43368A0 (en) | 1974-01-14 |
| NL7313668A (enrdf_load_stackoverflow) | 1974-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |