CS224904B1 - The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole - Google Patents
The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole Download PDFInfo
- Publication number
- CS224904B1 CS224904B1 CS476382A CS476382A CS224904B1 CS 224904 B1 CS224904 B1 CS 224904B1 CS 476382 A CS476382 A CS 476382A CS 476382 A CS476382 A CS 476382A CS 224904 B1 CS224904 B1 CS 224904B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- deoxy
- nitro
- talitol
- preparation
- galactitol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- 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 1
- PYMYPHUHKUWMLA-YUPRTTJUSA-N aldehydo-L-lyxose Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-YUPRTTJUSA-N 0.000 claims description 13
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 13
- 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
- 238000000034 method Methods 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-DHVFOXMCSA-N L-galactose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-DHVFOXMCSA-N 0.000 description 2
- GZCGUPFRVQAUEE-OMMKOOBNSA-N aldehydo-L-talose Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-OMMKOOBNSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002242 deionisation method Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 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 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
- 238000010009 beating Methods 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
- -1 diethyl alcohol Chemical compound 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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-L-talitolu a 1-deoxy-l-nitro-L-galaktitolu z L-lyxózy.The invention relates to a process for the preparation of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol from L-lyxose.
Příprava l-deoxy-l-nitro-alditolov sa uskutočňuje pomocou nitrometanovej syntézy. Táto sa prevádza tak, že sa pósoZ bí nitrometénom a metylátom sodným na aldozu kratšiu o jeden uhlíkový atom. Vzniká zmes sodných solí dvoch epimérnych 1-deoxy-l-nitro-alditoloV. Táto zmes sa rozpustí vo vodě a roztok sa zbaví sodných iónov na koloně vymieňača katiónov eluát z kolony sa zahustí a z alkoholického roztoku sa získajú krystalické látky 45 až 50& výtažku. /J.C.Sowden, H.O.L. Fischer, J.Am.Chem.Soc. 67,1963/1947^ Této reakcia bola niekoTkokrát preskúraaná za účelom zvýšenia výťažnosti produktov ale bez úspěchu. ,/H.H.Baer, Adv. Carbohyd.Chem.Biochem. 24, /1969/; J.C.Sowden, Adv.Carbohyd.Chem. 6, 291 /1951^The preparation of 1-deoxy-1-nitro-alditols is carried out by nitromethane synthesis. This is accomplished by beating nitromethene and sodium methylate to an aldose shorter by one carbon atom. A mixture of sodium salts of two epimeric 1-deoxy-1-nitro-alditol was formed. This mixture was dissolved in water and the solution was freed of sodium ions on a cation exchange column and the eluate from the column was concentrated and crystalline 45-50% yield was obtained from the alcoholic solution. /J.C.Sowden, H.O.L. Fischer, J. Am. This reaction was reviewed several times to increase the yield of the products but without success. , H. H. Baer, Adv. Carbohyd.Chem.Biochem. 24 (1969); J.C.Sowden, Adv.Carbohyd.Chem. 6, 291 (1951)
Zistili sme, že sodné soli 1-deoxy-l-nitró-L-talitol a 1-deoxy-l-nitro-L-galaktitol sa vo vodnom roztoku rozkladajú za vzniku L-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 /L-lyxóza/, zťažuje kryštalizáciu a samozřejmé znižuje výtažnosť reakcie. Uvedení autoři pokládali přítomnost L-lyxózy za nezřeagováný zbytok východzej látky. Navrhovaný spósob prí pravý 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro-L-galakti/ ř tolu zabraňuje uvoTneniu L-lyxozy a podstatné zvýši výtažnosť produktov, ktoré sú medziproduktami pri príprave L-talózy a L-galaktózy.We have found that the sodium salts of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol decompose in aqueous solution to form L-lyxose. This decomposition begins as soon as the sodium salts have dissolved in water and continue until the entire amount of solution has passed through the ion exchange column. The resulting lower aldose (L-lyxose) hinders crystallization and, of course, reduces the yield of the reaction. These authors considered the presence of L-lyxose as an unreacted residue of the starting material. The proposed manner at right 1-deoxy-L-nitro-L-talitolu and 1-deoxy-L-nitro-L-galacto / R Tolu prevents uvoTneniu L-lyxose and significantly increases the yield of products, which are intermediates in the preparation of L-talose and L-galactose.
Podstata vynálezu je, že sa zabráni rozkladu sodných solí 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro-L-galaktitolu na L-lyxózu tak, že sa sodné soli před deionizáciou rozpustia v zriedenej kyselině octovej. Tento roztok sa podrobí deionizécii cez vymieňač katiónov. Po zahuštění eluétu z kolony io-Jj224 904 nexu vykrystalizuje zmes 1-deoxy-l-nitro-L-talitolu a 1-deoxy-1-nitro-L-galaktitolu okolo 70 %, pričom neobsahuje žiadnu východziu L-lyxózu.The principle of the invention is to prevent the decomposition of the sodium salts of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol into L-lyxose by dissolving the sodium salts in dilute acetic acid prior to deionization . This solution is subjected to deionization through a cation exchanger. After concentrating the eluate from the io-J224 904 nex column, a mixture of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol crystallized to about 70%, containing no starting L-lyxose.
Výhodou navrhovaného spósobu přípravy 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro-L-galaktitolu je lepšia kryštalizácia nových produktov. Vzniklá reakčná zmes neobsahuje L-lyxózu, čím odpadne proces jej izolácie. Poskytuje přípravu výrobku o vysokej čistotě a výtažku, čím sa zlacňuje spósob přípravy.The advantage of the proposed process for the preparation of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol is that the new products are better crystallized. The resulting reaction mixture does not contain L-lyxose, thereby eliminating the process of isolation. It provides the preparation of a high purity product and an extract, thereby reducing the cost of preparation.
Příklad 1Example 1
Zmes L-lyxózy /50 g/ sa mieša s roztokom metylátu sodného připraveného rozpuštěním /10,5 g/ sodíka /450 g/ metylalkoholu a s nitrometanom /180 g/ pri 20°C po dobu 16 hodin. Vylúčené sodné soli 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro-L-galaktitolu áa odfiltruji!, premyjú raetylalkohom /100 ml/ a rozpustia v 10% kyselina octovéj /650 ml/. Roztok sa deionizuje cez kolonu naplnenú ionexom /vymienačoa katiónov/ o rozmeroch kolony dížky 60 a priemeru 4 centimetre. Eluát z kolony sa zahustí na kašovitý zvyšok, ktorý sa rozpustí za varu v 96% etylalkohole /200 ml/. Po ochladení roztoku na 0°C vykryštalizuje 39 g zmesi 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro-L-galaktitolu. Po dalšej kryštalizácii matečného lúhu sa zíaka dalších 10 g produktu. Celkove sa získalo 49 g zmesi 1-deoxy-l-nitro-L-talitolu a 1-deoxy-l-nitro -L-galaktitolu, ktoré neobsahovali žiadnu L-lyxózu. Výťažok na L-lyxózu je 70%.The mixture of L-lyxose (50 g) is mixed with a solution of sodium methylate prepared by dissolving (10.5 g) sodium (450 g) methanol and nitromethane (180 g) at 20 ° C for 16 hours. The precipitated sodium salts of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol are filtered, washed with diethyl alcohol (100 ml) and dissolved in 10% acetic acid (650 ml). The solution is deionized through a column packed with an ion exchange resin (cation exchanger) having a column size of length 60 and a diameter of 4 centimeters. The eluate from the column is concentrated to a slurry which is dissolved in boiling in 96% ethyl alcohol (200 ml). After cooling the solution to 0 ° C, 39 g of a mixture of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol crystallize. After further crystallization of the mother liquor, an additional 10 g of product is collected. In total, 49 g of a mixture of 1-deoxy-1-nitro-L-talitol and 1-deoxy-1-nitro-L-galactitol were obtained which contained no L-lyxose. The yield on L-lyxose is 70%.
Vynález má rozsiahle využitie pri přípravě 1-deoxy-l-nitro-Ltalitolu a l-deoxy-l-nitro-L-galaktitolu, ktoré sú medziproduktom pri príprave L-talózy, L-galaktózy, ktoré sa používajú' pri štúdiu biochemických pochodov a v medecíne.The invention has extensive application in the preparation of 1-deoxy-1-nitro-L -talitol and 1-deoxy-1-nitro-L-galactitol, which are intermediates in the preparation of L-talose, L-galactose, used in the study of biochemical processes and medecine.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476382A CS224904B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476382A CS224904B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224904B1 true CS224904B1 (en) | 1984-02-13 |
Family
ID=5391115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS476382A CS224904B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS224904B1 (en) |
-
1982
- 1982-06-25 CS CS476382A patent/CS224904B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5015296A (en) | Continuous epimerization of sugars, in particular D-arabinose to D-ribose | |
| RU2008149696A (en) | METHOD FOR PRODUCING BISPHENOL A HIGH PURITY AND PRODUCTION INSTALLATION | |
| CN102241601A (en) | Preparation technology for iminodiacetic acid | |
| US2606186A (en) | Preparation of methyl glucoside | |
| US4294766A (en) | Preparation of pure potassium ribonate and ribonolactone | |
| US4536221A (en) | Process for preparing lactulose from lactose, in the form of a syrup or a crystalline product | |
| CS224904B1 (en) | The preparation of the 1-deoxy-nitro-d-talitol and the 1-deoxy-1-nitro-d-galactitole | |
| DE69933578D1 (en) | PREPARATION OF HIGH-PURITY L-RIBOSE FROM L-ARABINOSE | |
| Sowden | A Convenient Method of Preparing 2-Deoxy-D-ribose1 | |
| US4447615A (en) | Process for the purification of nicotinic acid amide I | |
| CS224905B1 (en) | The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol | |
| CS224903B1 (en) | The production of 1-deoxy-1-nitro-d-talitol and 1-deoxy-1-nitro-d-galactitole | |
| US5616769A (en) | Method for purifying O,S-dimethyl N-acetylphosphoramidothioate | |
| Schaffer | Improved Synthesis of Sodium D-glucuronate-6-C14 and of D-glucose-6-C14 | |
| JP2023095750A (en) | Method for recycling taurine mother liquor | |
| RU2404159C2 (en) | Method for synthesis of dihydrate of 3-(2,2,2-trimethylhydrazinium)-propionate | |
| US4447614A (en) | Process for the purification of nicotinic acid amide | |
| JP2006516148A (en) | Method for extracting 2-keto-L-gulonic acid (KGA) from a polar, preferably aqueous solvent | |
| US2779760A (en) | Lithium maltobionate and process for making same | |
| CS227527B1 (en) | Method of preparing l-galactose | |
| US3709912A (en) | Process for preparing d-ribonolactone | |
| KR20150082317A (en) | Methods for decolorizing compositions comprising betaines | |
| CS224998B1 (en) | The preparation of 1-deoxy-1-nitro-d-gulithole and 1-deoxy-1-nitro-d-iditol | |
| US4228081A (en) | Separation of isomers | |
| GB880573A (en) | Process for the manufacture of the tetrahydrate or salts of cocarboxylase |