CS224905B1 - The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol - Google Patents
The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol Download PDFInfo
- Publication number
- CS224905B1 CS224905B1 CS476282A CS476282A CS224905B1 CS 224905 B1 CS224905 B1 CS 224905B1 CS 476282 A CS476282 A CS 476282A CS 476282 A CS476282 A CS 476282A CS 224905 B1 CS224905 B1 CS 224905B1
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- CS
- Czechoslovakia
- Prior art keywords
- deoxy
- nitro
- glucitol
- mannitol
- arabinose
- Prior art date
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- HOFCJTOUEGMYBT-VANKVMQKSA-N (2s,3s,4s,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-VANKVMQKSA-N 0.000 title claims description 13
- HOFCJTOUEGMYBT-BXKVDMCESA-N (2s,3s,4s,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-BXKVDMCESA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 5
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims description 12
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-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 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000002242 deionisation method Methods 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 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
- WQZGKKKJIJFFOK-JFNONXLTSA-N L-mannopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-JFNONXLTSA-N 0.000 description 1
- -1 L-mannose saccharides Chemical class 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
- 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
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Description
Vynález sa týká spdsobu přípravy 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu z L-arabinózy.The invention relates to a process for the preparation of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol from L-arabinose.
Tieto látky sú medziproduktami pri príprave L-glukózy a L-manózy. Vyrábajú sa pósobením nitrometánu a metylátu sodného na L-arabinózu látku kratšiu o jeden uhlíkový atom· Vzniká zmes sodných solí dvoch epimérnych aldóz, l-deoxy-l-nitro-L-glucitol a 1-deoxy-l-nitro-L-manitol. Táto zmes sa rozpustí vo vodě roztok sa zbaví sodných ionov na kolóne vymieftača katiónov, eluát z kolony sa zahustí a kryStalizéciou vznikajú produkty 45 až 50 % výtažku. /J.C.Sowden, H.O. Fisclir, J.Am.Chem.Soc. 67.1963/1947/^ Této reakcia bola niekoTko krát modifikovaná avšak výťažok reakcie sa nezvýšil /J.C. Sowden., Adv.Carbohyd.Chem. 6,291 /1951^These compounds are intermediates in the preparation of L-glucose and L-mannose. They are produced by reacting nitromethane and sodium methylate on L-arabinose with a shorter one carbon atom. This mixture is dissolved in water, the solution is freed of sodium ions on a cation exchange column, the eluate from the column is concentrated and crystallization yields 45-50% yields. /J.C.Sowden, H.O. Fisclir, J. Am. 67.1963 (1947) This reaction was modified several times but the yield of the reaction did not increase (J.C.). Sowden., Adv.Carbohyd.Chem. 6,291 (1951)
Zistili sme, že sodné o.oli l-deoxy-l-nitro-L-glucitol a 1-deoxy-l-nitro-L-raanitol sa vo vodnom roztoku rozkladajú za vzniku východzej L-arahinózy. Tento rozklad zašne prebiehať akonáhle sa sodné soli rozpustia vo vodě a trvá pokial’ celé množstvo roztoku nepřetečie cez ionexovú kolonu. Vzniklé nižšia aldóza /L-arabinóza/, sťažuje kryštalizáciu a samozřejmé znižuje výťažnosť reakcie. Navrhovaný spdsob přípravy 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu zabraňuje uvoTneniu L-arabinózy a podstatné zvýši výťažnosť produktov.We have found that the sodium salts of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol decompose in aqueous solution to give the starting L-arahinose. This decomposition will proceed as soon as the sodium salts are dissolved in water and it lasts until the entire amount of the solution overflows through the ion exchange column. The resulting lower aldose (L-arabinose) hinders crystallization and, of course, reduces the yield of the reaction. The proposed method of preparing 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol prevents the release of L-arabinose and substantially increases the yield of the products.
Podstata vynálezu je, že sa zabráni rozkladu sodných solí 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu na L-arabinózu tak, že sa sodné soli před deionizáciou rozpustia v zriedenej kyselině octovej. Tento roztok sa podrobí deionizácii cez vymieftač kationov. Po zahuštění eluátu z kolony ionexu vykryštalizuje zmes 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu okolo 70#, pričom neobsahuje žiadnu východziu L-arabinózu.The principle of the invention is to prevent the decomposition of the sodium salts of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol into L-arabinose by dissolving the sodium salts in dilute acetic acid prior to deionization . This solution is subjected to deionization through a cation exchanger. Upon concentration of the eluate from the ion exchange column, a mixture of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol crystallizes around 70%, containing no starting L-arabinose.
Výhodou navrhovaného spósobu přípravy l-deoxy-l-nitro-L224 905The advantage of the proposed process for the preparation of 1-deoxy-1-nitro-L224 905
-glucitolu a 1-deoxy-l-nitro-L-manitolu je* lepšia kryštalizácia nových produktov, Vzniklá reakčná zmes neobsahuje L-arabinózu, čím odpadne proces jej izolácie· Poskytuje přípravu výrobku o vysokej čistotě a výtažku, čím sa zlacňuje spósob přípravy.-glucitol and 1-deoxy-1-nitro-L-mannitol is a better crystallization of the new products. The resulting reaction mixture does not contain L-arabinose, thus eliminating the process of its isolation.
Příklad 1Example 1
Zmes L-arabinózy. /150 g/ sa mieša s roztokom metylátu sodného připraveného rozpuštěním /31,5 g/ sodíka v /1350 ml/ metylalkoholu a s nitrometanom /540 ml/ pri 2O°C po dobu 16 h.L-arabinose mixture. (150 g) was stirred with a solution of sodium methylate prepared by dissolving (31.5 g) sodium in (1350 ml) methanol and nitromethane (540 ml) at 20 ° C for 16 h.
Vylúčené sodné soli 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro L-manitolu sa odfiltrujú, premyjú metylalkoholom /250 ml/ a rozpustia sa v 10% kyselině octovej /2000 ml/. Roztok sa deionizuje cez kolonu naplnenú ionomeničom /vymienačom katiohov/ rozmaroch kolony dl’žky 80 a priemeru 4 centimetre. Eluát z kolony sa zahustí na kašovitý zvyšok, ktorý sa riedi 96% etylalkoholom /600 ml/ a zmes sa ochladí na 0°C.The precipitated sodium salts of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro L-mannitol are filtered off, washed with methanol (250 ml) and dissolved in 10% acetic acid (2000 ml). The solution is deionized through a column packed with an ion exchanger / catheter exchanger / caprices of a length of 80 and a diameter of 4 centimeters. Concentrate the eluate from the column to a slurry which is diluted with 96% ethyl alcohol (600 mL) and cooled to 0 ° C.
Vykrystalizuje 128 g zmesi 1-ďeoxy-lnitro-L-glucitolu a 1-deoxy-1-nitro-L-manitolu. Po zahuštění matečného lúhu a ďalšej kryštalizácie sa získá dalších 16 g zmesi produktov. Celkove sa získá 144 g zmesi 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu, ktoré neobsahujú žiadnu L-arabinózu. Výťažok na L-arabinózu je 68,5 %·128 g of a mixture of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol crystallize. After concentration of the mother liquor and further crystallization, an additional 16 g of product mixture is obtained. In total, 144 g of a mixture of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol are obtained which contain no L-arabinose. L-arabinose yield is 68.5% ·
Vynález má rozsiahle využitie pri príprave 1-deoxy-l-nitro-L-glucitolu a 1-deoxy-l-nitro-L-manitolu, ktoré sú medziproduktami pri výrobě ťažko dostupných vzácných sacharidov L-glukózy a L-manozy, ktoré sa používajú pri štúdiu biochemických pochodov a v medecíne.The invention has extensive application in the preparation of 1-deoxy-1-nitro-L-glucitol and 1-deoxy-1-nitro-L-mannitol, which are intermediates in the production of the scarce rare L-glucose and L-mannose saccharides used in the study of biochemical processes and in medicine.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476282A CS224905B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS476282A CS224905B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224905B1 true CS224905B1 (en) | 1984-02-13 |
Family
ID=5391106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS476282A CS224905B1 (en) | 1982-06-25 | 1982-06-25 | The preparation of the 1-deoxy -1-nitro-l-glucitol and the 1-deoxy-1-nitro-l-mannitol |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS224905B1 (en) |
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1982
- 1982-06-25 CS CS476282A patent/CS224905B1/en unknown
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