CS224903B1 - The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole - Google Patents
The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole Download PDFInfo
- Publication number
- CS224903B1 CS224903B1 CS476482A CS476482A CS224903B1 CS 224903 B1 CS224903 B1 CS 224903B1 CS 476482 A CS476482 A CS 476482A CS 476482 A CS476482 A CS 476482A CS 224903 B1 CS224903 B1 CS 224903B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- deoxy
- nitro
- talitol
- lyxose
- galactitol
- Prior art date
Links
- HOFCJTOUEGMYBT-KAZBKCHUSA-N (2r,3s,4r,5r)-6-nitrohexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C[N+]([O-])=O HOFCJTOUEGMYBT-KAZBKCHUSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims 2
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 claims description 13
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 13
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 13
- HOFCJTOUEGMYBT-KCDKBNATSA-N (2r,3s,4r,5s)-6-nitrohexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C[N+]([O-])=O HOFCJTOUEGMYBT-KCDKBNATSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GZCGUPFRVQAUEE-KAZBKCHUSA-N aldehydo-D-talose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KAZBKCHUSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká spósobu přípravy 1-deoxy-l-nitro-D-talitolu a 1-deoxy-l-nitro-D-galaktitolu z D-lyxózy.The invention relates to a process for the preparation of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol from D-lyxose.
Příprava 1-deoxy-l-nitroalditolov sa uskutočňuje pomocou nitrometanovej syntézy· Táto sa prevádza tak, že sa pósobí nitrometánom a metylátom sodným na aldózu kratšiu o jeden uhlíkový atom. Vzniká zmes sodných solí dvoch epimérnych 1-deoxy-l-nitroalditolov. Táto zmes sa rozpustí vo vodě a roztok sa zbaví sodných iónov na koloně vymieňača kationov eluát z kolony sa zahustí a z alkoholického roztoku sa získajú kryátalické látky 45 až 50% výtažku./J.C.Sowden, H.O.L· Fischer, J.Am.Chem.Soc. 67,1963/1947$ Táto reakcia bola niekoTkokrát preskúmaná za účelom zvýšenia výtažnosti produktov ale bez úspěchu. /H.H.Baert Adv. Carbohyd.Chem.Biochem. 24, 67/1969/; J.C.Sowden, Adv.Carbohyd.Chem. 6, 291 /1951$The preparation of 1-deoxy-1-nitroalditols is carried out by nitromethane synthesis. This is carried out by treatment with nitromethane and sodium methylate to give an aldose shorter by one carbon atom. A mixture of sodium salts of two epimeric 1-deoxy-1-nitroalditols is formed. This mixture is dissolved in water and the solution is freed from sodium ions on a cation exchange column, the eluate from the column is concentrated, and the alcoholic solution yields crystals of 45 to 50% yield./ JCSowden, HOL · Fischer, J.Am.Chem.Soc. 67,1963 / 1947 $ This reaction has been reviewed several times to increase product yield, but without success. / HH Baer t Adv. Carbohyd.Chem.Biochem. 24, 67 (1969); JCSowden, Adv.Carbohyd.Chem. 6,291 / 1951 $
Zistili sme, že sodné soli 1-deoxy-l-nitro-D-talitol a 1-deoxy-l-nitro-D-galaktitol sa vo vodnom roztoku rozkládájú za vzniku D-lyxózy. Tento rozklad začne prebiehať akonáhle sa sodné soli rozpustia vo vodě a trvá pokial’ celé množstvo roztoku nepretečie cez ionexovú kolonu. Vzniklá nižšia aldóza /D-lyxóza/, ztažuje kryštalizáciu a samozřejmé znižuje výťažnost reakcie. Uvedení autoři pokládali přítomnost D-lyxózy za nezřeagovaný zbytok východzej látky. Navrhovaný spósob prí pravý 1-deoxy-l-nitro-D-talitolu a 1-deoxy-l-nitro-D-galaktitolu zabraňuje uvoTneniu D-lyxózy a podstatné zvýši výťažnost produktov, ktoré sú medziproduktami pri príprave D-talózy a D-galaktózy.We have found that the sodium salts of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol decompose in aqueous solution to form D-lyxose. This decomposition starts as soon as the sodium salts dissolve in water and it lasts until the entire amount of solution flows through the ion exchange column. The resulting lower aldose (D-lyxose) hinders crystallization and, of course, reduces the yield of the reaction. These authors considered the presence of D-lyxose as an unreacted residue of the starting material. The proposed process for the preparation of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol prevents the release of D-lyxose and significantly increases the yield of intermediate products in the preparation of D-talose and D-galactose .
Podstata vynálezu je, že sa zabráni rozkladu sodných solí 1-deoxy-l-nitro-D-talitolu a 1-deoxy-l-nitro-D-galaktitolu na D-lyxózu tak, že sa sodné soli před deionizáciou rpzpustia v zriedenej kyselině octovéj. Tento roztok sa podrobí deioni224 903 zócii cez vymieňač katiónov. Po zahuštění eluátu z kolony ionexu vykrystalizuje zmes 1-deoxy-l-nitro-D-talitolu a 1-deoxy -1-nitro-D-galaktitolu okolo 70%» pričom neobsahuje žiadnu východziu D-lyxózu.SUMMARY OF THE INVENTION The principle of the invention is to prevent the decomposition of sodium salts of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol into D-lyxose by dissolving the sodium salts in dilute acetic acid before deionization. . This solution is subjected to a deion 1224 903 zone through a cation exchanger. After concentrating the eluate from the ion exchange column, a mixture of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol crystallizes to about 70% without any starting D-lyxose.
Výhodou navrhovaného spósobu přípravy 1-deoxy-l-nitroD-talitolu a 1-deoxy-l-nitro-D-galaktitolu je lepšia kryštalizácia nových produktov# Vzniklá reakčná zmes neobsahuje D-lyxózu,.‘čím odpadne proces jej izolácie. Poskytuje přípravu výrobku o vysokéj čistotě a výťažku, čím sa zlacňuje spósob přípravy#The advantage of the proposed process for the preparation of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol is better crystallization of the new products # The resulting reaction mixture does not contain D-lyxose, thus eliminating the isolation process. Provides product preparation with high purity and yield, making the preparation process cheaper #
Příklad 1Example 1
Zmes D-lyxózy /100 g/ sa mieša s roztokom metylátu sodného připraveného rozpuštěním /11 g/ sodíka v /900 g/ metylalkoholu a s nitrometanom /360 g/ pri 20°C, po dobu 16 h. Vylúčené sodné soli 1-deoxy-l-nitro-D-talitolu a 1-deoxy-l-nitro-D-galaktitolu sa odfiltrujú, premyjú metylalkoholom /300 ml/ a rozpustia v 10% kyselině octovéj v /1300 ml/. Roztok sa deionizuje cez kolonu naplnenú ionexom /vymienačom katiónov/ 0 rozmeroch dížky 60 a priemeru 4 centimetre# Eluát z kolony sa zahustí na kašovitý zvyšok, ktorý sa rozpustí za varu v 96% etylalkohole /400 ml/. Po ochladení roztoku na 0°C vykrystalizuje 79 g zmesi 1-deoxy-l-nitro-D-talitolu a 1-deoxy-l-nitro-D-galaktitolu. Po dalšej kryštalízácii matečného lúhu sa získá dalších 20,5 g produktu. Celkove sa získá 99,5 g zmesi 1-deoxy-l-nitroalditolov, ktoZ ré neobsahovali žiadnu D-lyxozu. Výťažok na D-lyxózu je 71%·The mixture of D-lyxose (100 g) is mixed with a solution of sodium methylate prepared by dissolving (11 g) sodium in (900 g) methanol and nitromethane (360 g) at 20 ° C for 16 h. The precipitated sodium salts of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol are filtered off, washed with methanol (300 ml) and dissolved in 10% acetic acid in (1300 ml). The solution is deionized through a column packed with an ion exchanger / cation exchanger ( 0 in 60 mm in diameter and 4 centimeters in diameter). The column eluate is concentrated to a slurry which is dissolved in boiling in 96% ethyl alcohol (400 ml). After cooling the solution to 0 ° C, 79 g of a mixture of 1-deoxy-1-nitro-D-talitol and 1-deoxy-1-nitro-D-galactitol crystallize. An additional 20.5 g of product is obtained after further crystallization of the mother liquor. A total of 99.5 g of a mixture of 1-deoxy-1-nitroalditols having no D-lyxose was obtained. D-lyxose yield 71% ·
Vynález má rozsiahle využitie pri príprave 1-deoxy-lhitro-Dtalitolu a 1-deoxy-l-nitro-D-galaktitolu, ktoré sú medziproduktom pri príprave D-talózy, D-galaktózy, ktoré sa používajú pri štúdiu biochemických pochodov a v medeeíne.The invention has extensive application in the preparation of 1-deoxy-lhitro-Dtalitol and 1-deoxy-1-nitro-D-galactitol, which are intermediates in the preparation of D-talose, D-galactose, used in the study of biochemical processes and in medine.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476482A CS224903B1 (en) | 1982-06-25 | 1982-06-25 | The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476482A CS224903B1 (en) | 1982-06-25 | 1982-06-25 | The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224903B1 true CS224903B1 (en) | 1984-02-13 |
Family
ID=5391130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS476482A CS224903B1 (en) | 1982-06-25 | 1982-06-25 | The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS224903B1 (en) |
-
1982
- 1982-06-25 CS CS476482A patent/CS224903B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Sowden et al. | The condensation of nitromethane with D-and L-arabinose: preparation of L-glucose and L-mannose | |
| Schaffer | Improved Synthesis of Sodium D-glucuronate-6-C14 and of D-glucose-6-C14 | |
| WO1984000759A1 (en) | Desoxyuridine derivatives, processes for their preparation and their use as pharmaceuticals | |
| Bílik | Reactions of Saccharides Catalyzed by Molybdate Ions. III.* Preparation of L-Glucose by Epimerization of L-Mannose or L-Mannose Phenylhydrazone | |
| US4294766A (en) | Preparation of pure potassium ribonate and ribonolactone | |
| JP4865128B2 (en) | High purity production of L-ribose from L-arabinose | |
| CS224903B1 (en) | The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole | |
| US3064003A (en) | Carboxylic acid derivatives of sub- | |
| Frush et al. | Preparation of D-Arabinose-1-C™ and D-Ribose-lC | |
| CS224905B1 (en) | The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol | |
| US4667054A (en) | Process for producing optically active valine | |
| CS224904B1 (en) | The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole | |
| JPS61212592A (en) | Production of d-ribose | |
| SU1328290A1 (en) | Method of producing cesium mercaptobenzothazoleundecahydrododecaborate | |
| US2480785A (en) | Production of sugar c-nitroalcohols | |
| CS227527B1 (en) | Method of preparing l-galactose | |
| CS225526B1 (en) | Preparation of l-manose | |
| CS224998B1 (en) | The preparation of 1-deoxy-1-nitro-d-gulithole and 1-deoxy-1-nitro-d-iditol | |
| RU2052447C1 (en) | Method for production of pentaerytritol | |
| US4263454A (en) | Lithium ribonate, lithium arabonate and the preparation and purification of these salts | |
| US3207782A (en) | Process for crystallization of alkali metal glutamates | |
| SU407878A1 (en) | METHOD FOR CLEANING POTASSIUM | |
| US3057869A (en) | 7-chloro-4-hydroxy-6-quinoline-sulfonamide | |
| RU1806135C (en) | Method of thiourea synthesis | |
| JPH06321979A (en) | Production of lactulose |