CH417630A - Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern - Google Patents
Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von ButantetrolesternInfo
- Publication number
- CH417630A CH417630A CH1086362A CH1086362A CH417630A CH 417630 A CH417630 A CH 417630A CH 1086362 A CH1086362 A CH 1086362A CH 1086362 A CH1086362 A CH 1086362A CH 417630 A CH417630 A CH 417630A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclic
- ketals
- acetals
- isopropylidene
- threit
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 8
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical class OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 title description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 4
- YCPOZVAOBBQLRI-UHFFFAOYSA-N treosulfan Chemical compound CS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O YCPOZVAOBBQLRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- -1 methanesulfonyl halide Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 3
- 229910010084 LiAlH4 Inorganic materials 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- KQEGLTLWSXUFMC-CRCLSJGQSA-N (2S,3R)-2,3-bis(hydroxymethyl)oxetan-3-ol Chemical compound C1[C@@](CO)(O)[C@@H](O1)CO KQEGLTLWSXUFMC-CRCLSJGQSA-N 0.000 description 2
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- INVRLGIKFANLFP-PHDIDXHHSA-N [(4r,5r)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)O[C@H](CO)[C@@H](CO)O1 INVRLGIKFANLFP-PHDIDXHHSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- PDTRBCTYOYMYKK-RFIDALOWSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate;(2r,3r)-2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC.CC[C@](O)(C(O)=O)[C@](O)(CC)C(O)=O PDTRBCTYOYMYKK-RFIDALOWSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- YTBSYETUWUMLBZ-UHFFFAOYSA-N D-Erythrose Natural products OCC(O)C(O)C=O YTBSYETUWUMLBZ-UHFFFAOYSA-N 0.000 description 1
- YTBSYETUWUMLBZ-IUYQGCFVSA-N D-erythrose Chemical compound OC[C@@H](O)[C@@H](O)C=O YTBSYETUWUMLBZ-IUYQGCFVSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical class OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- 206010056474 Erythrosis Diseases 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 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
- INVRLGIKFANLFP-WDSKDSINSA-N [(4s,5s)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)O[C@@H](CO)[C@H](CO)O1 INVRLGIKFANLFP-WDSKDSINSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- NDEIPVVSKGHSTL-UHFFFAOYSA-N butane-1,1,1,2-tetrol Chemical class CCC(O)C(O)(O)O NDEIPVVSKGHSTL-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33247/61A GB976534A (en) | 1961-09-15 | 1961-09-15 | Cyclic 2,3-o-acetals and 2,3-o-ketals of butanetetrol esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH417630A true CH417630A (de) | 1966-07-31 |
Family
ID=10350441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1086362A CH417630A (de) | 1961-09-15 | 1962-09-12 | Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3246012A (en, 2012) |
| BE (1) | BE622353A (en, 2012) |
| CH (1) | CH417630A (en, 2012) |
| DK (1) | DK114489B (en, 2012) |
| ES (1) | ES280760A1 (en, 2012) |
| FR (2) | FR1575503A (en, 2012) |
| GB (1) | GB976534A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948953A (en) * | 1969-08-05 | 1976-04-06 | Texaco Inc. | Dioxolane derivatives having surfactant properties |
| US4060532A (en) * | 1972-03-15 | 1977-11-29 | Ici United States Inc. | Halogenated dioxolane tranquilizers |
| US3996376A (en) * | 1972-03-28 | 1976-12-07 | Ici United States Inc. | Halogenated dioxolane tranquilizers |
| US4591601A (en) * | 1985-04-12 | 1986-05-27 | Mcneilab, Inc. | Anticonvulsant dioxolane methane sulfamates |
| CN103896903A (zh) * | 2012-12-26 | 2014-07-02 | 北京奥得赛化学股份有限公司 | 制备和纯化2,3-o-异亚丙基苏糖醇的方法 |
| WO2019043587A2 (en) | 2017-08-31 | 2019-03-07 | Fresenius Kabi Oncology Ltd. | PROCESS FOR THE PREPARATION OF TREOSULFAN |
-
0
- BE BE622353D patent/BE622353A/xx unknown
-
1961
- 1961-09-15 GB GB33247/61A patent/GB976534A/en not_active Expired
-
1962
- 1962-09-10 FR FR1575503D patent/FR1575503A/fr not_active Expired
- 1962-09-12 DK DK398062AA patent/DK114489B/da unknown
- 1962-09-12 CH CH1086362A patent/CH417630A/de unknown
- 1962-09-13 ES ES0280760A patent/ES280760A1/es not_active Expired
- 1962-12-07 FR FR917832A patent/FR2393M/fr not_active Expired
-
1964
- 1964-03-25 US US354778A patent/US3246012A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK114489B (da) | 1969-07-07 |
| BE622353A (en, 2012) | |
| GB976534A (en) | 1964-11-25 |
| ES280760A1 (es) | 1963-02-01 |
| FR2393M (fr) | 1964-03-09 |
| US3246012A (en) | 1966-04-12 |
| FR1575503A (en, 2012) | 1969-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH417630A (de) | Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern | |
| AT391866B (de) | Verfahren zur herstellung neuer s-triazolo (1,5-a) pyrimidine | |
| DE1912941C3 (de) | 1 -Phenyl^-amino-e-methoxypyridaziniumsalze | |
| AT202152B (de) | Verfahren zur Herstellung von neuen Dimethylaminopropylidenthiaxanthenen. | |
| DE1918253A1 (de) | Verbessertes Verfahren zur Herstellung von 3-Hydroxyisoxazolverbindungen | |
| AT236969B (de) | Verfahren zur Herstellung neuer cyclischer 2,3-O-Acetale und 2,3-O-Ketale von Butan-1,2,3,4-tetrol-1,4-di-(methansulfonat) | |
| AT346838B (de) | Verfahren zur herstellung von neuen optisch aktiven anthracyclinonen | |
| AT260920B (de) | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen | |
| AT266075B (de) | Verfahren zur Herstellung von neuen Sulfonaniliden und deren Säureadditions- und Metallsalzen | |
| AT269886B (de) | Verfahren zur Herstellung neuer Benzomorphanderivate und ihrer Salze | |
| DE952715C (de) | Verfahren zur Herstellung neuer antihistaminwirksamer basischer AEther | |
| AT204045B (de) | Verfahren zur Herstellung von neuen Piperazinderivaten und von deren Salzen | |
| AT371448B (de) | Verfahren zur herstellung von neuen cis-4a-phenyl -isochinolin-derivaten und ihren saeureadditionssalzen | |
| DE1249851B (de) | Morel Ariesheim (Schweiz) j Verfahren zur Herstellung neuer Phenoxyessigsäure amide | |
| AT258280B (de) | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen | |
| DE869965C (de) | Verfahren zur Zerlegung der diastereomeren Formen von dl-Aminodiolen | |
| AT203015B (de) | Verfahren zur Herstellung von neuen 1-(p-Butoxyphenyl)-3-(p-pyridylphenyl)-2-thioharnstoffen | |
| AT213883B (de) | Verfahren zur Herstellung von neuen 3-Phenyl-3-pyrrolidinol-Verbindungen | |
| DE1050763B (de) | Synthese von Vitamin-A-Säure und ihren Estern | |
| AT204041B (de) | Verfahren zur Herstellung von neuen Phenthiazinderivaten | |
| AT226707B (de) | Verfahren zur Herstellung von neuen 11b-Benzo-(a)-chinolizinderivaten | |
| AT234691B (de) | Verfahren zur Herstellung von neuen Piperidinderivaten | |
| AT360007B (de) | Verfahren zur herstellung von 2-(phenylamino)- imidazolin-(2)derivaten und deren salzen | |
| AT235268B (de) | Verfahren zur Herstellung sekundärer bzw. tertiärer Amine und deren Additionssalze mit Säuren | |
| AT228804B (de) | Verfahren zur Herstellung von Thionothiolphosphorsäureestern |