CH381666A - Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen - Google Patents
Verfahren zur Herstellung von Derivaten von polyhydrischen AlkoholenInfo
- Publication number
- CH381666A CH381666A CH7251559A CH7251559A CH381666A CH 381666 A CH381666 A CH 381666A CH 7251559 A CH7251559 A CH 7251559A CH 7251559 A CH7251559 A CH 7251559A CH 381666 A CH381666 A CH 381666A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- preparation
- dimethanesulfonyl
- choh
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000005846 sugar alcohols Polymers 0.000 title description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- -1 2,3,4,5 - tetraacetyl - mannitol Chemical compound 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 239000012345 acetylating agent Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BQBLBKUCNKKTIO-PAZDGXDMSA-N C(C)(=O)[C@@](C(O)S(=O)(=O)C)(O)[C@](O)([C@](O)(C(O)S(=O)(=O)C)C(C)=O)C(C)=O Chemical compound C(C)(=O)[C@@](C(O)S(=O)(=O)C)(O)[C@](O)([C@](O)(C(O)S(=O)(=O)C)C(C)=O)C(C)=O BQBLBKUCNKKTIO-PAZDGXDMSA-N 0.000 description 2
- UQDYPNQNGOMZGU-LAXKNYFCSA-N CS(=O)(=O)C([C@H](O)[C@H](O)C(O)S(=O)(=O)C)O Chemical compound CS(=O)(=O)C([C@H](O)[C@H](O)C(O)S(=O)(=O)C)O UQDYPNQNGOMZGU-LAXKNYFCSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DSJWYUXLLANNFA-MRTQZFPLSA-N (2s,3s,4s,5s)-1,6-bis(methylsulfonyl)hexane-1,2,3,4,5,6-hexol Chemical compound CS(=O)(=O)C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)S(C)(=O)=O DSJWYUXLLANNFA-MRTQZFPLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LVIIWCFEMTYCDV-OXYCZDQYSA-N CC([C@@](C(O)S(C)(=O)=O)([C@@](C(O)S(C)(=O)=O)(C(C)=O)O)O)=O Chemical compound CC([C@@](C(O)S(C)(=O)=O)([C@@](C(O)S(C)(=O)=O)(C(C)=O)O)O)=O LVIIWCFEMTYCDV-OXYCZDQYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13081/58A GB891466A (en) | 1958-04-24 | 1958-04-24 | New methane sulphonic acid esters of polyols |
| GB3414858 | 1958-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH381666A true CH381666A (de) | 1964-09-15 |
Family
ID=26249527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7251559A CH381666A (de) | 1958-04-24 | 1959-04-24 | Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH381666A (en)) |
| FR (3) | FR578M (en)) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU175923B (en) * | 1978-05-03 | 1980-11-28 | Gyogyszerkutato Intezet | Process for preparing 1,6-di-o-methanesulphonyl-3,4-di-o-methyl-d-mannitol |
| HU176216B (en) * | 1978-05-11 | 1981-01-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing terminally bifuntional xylite derivatives of citostatic activity |
-
1959
- 1959-04-24 CH CH7251559A patent/CH381666A/de unknown
-
1960
- 1960-08-31 FR FR837393A patent/FR578M/fr active Active
- 1960-08-31 FR FR837394A patent/FR656M/fr active Active
- 1960-08-31 FR FR837395A patent/FR657M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR656M (en)) | 1961-07-10 |
| FR578M (en)) | 1961-06-05 |
| FR657M (en)) | 1961-07-10 |
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