CS225577B1 - Preparation of 1-deoxy-1-nitro-l-gulithol and 1-deoxy-1-nitro-6-iditol - Google Patents
Preparation of 1-deoxy-1-nitro-l-gulithol and 1-deoxy-1-nitro-6-iditol Download PDFInfo
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- CS225577B1 CS225577B1 CS721982A CS721982A CS225577B1 CS 225577 B1 CS225577 B1 CS 225577B1 CS 721982 A CS721982 A CS 721982A CS 721982 A CS721982 A CS 721982A CS 225577 B1 CS225577 B1 CS 225577B1
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- Prior art keywords
- deoxy
- nitro
- iditol
- preparation
- gulitol
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- 238000002360 preparation method Methods 0.000 title claims description 8
- 229960002920 sorbitol Drugs 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 claims description 4
- 229930195726 aldehydo-L-xylose Natural products 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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-ZNVMLXAYSA-N L-idopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-ZNVMLXAYSA-N 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
POPIS VYNALEZU K AUTORSKÉMU OSVĚDČENU) ČESKOSLOVENSKÁ SOCIALISTICKÁDESCRIPTION FOUND TO COPYRIGHT CERTIFICATE) CZECHOSLOVAK SOCIALIST
REPUBLIKA (19) 225577REPUBLIC (19) 225577
(11) (BIJ(11) (BIJ
ÚŘAD PRO VYNÁLEZYA OBJEVY (23) Výstavná priorita(22) Přihlášené 11 10 82(21) PV 7219-82 (51) Int. Cl.3 C 07 C 79/18 (40) Zverejnené 24 06 83 (45) Vydané 30 09 85 (75) KUBALA JOZEF ing., ČAPLOVIČ JÁN ing„INVENTORY OFFICE DISCOVERY (23) Exhibition Priority (22) Entries 11 10 82 (21) PV 7219-82 (51) Int. Cl.3 C 07 C 79/18 (40) Published 24 06 83 (45) Published 30 09 85 (75) KUBALA JOZEF ing., ČAPLOVIČ JÁN ing
Autor vynálezu ŠVEC JOZEF ing., BRATISLAVA (54) Spfisob přípravy 1-deoxy-l-nitro-L-gulitolu a l-deoxy-l-nitro-L--iditoluThe inventor of ŠVEC JOZEF ing., BRATISLAVA (54) Preparation of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol
Vynález sa týká spósobu přípravy 1-deoxy--1-nitro-L-gulitolu a 1-deoxy-l-nitro-L-iditolu. 1-deoxy-l-nitroalditoly připravili nitroroe-tanovou syntézou [J. C. Sowden, H. O. L.Fischer: J. Am. Chem. Soc. 67, 1713 (1945),J. C. Sowden: Adv. Carbohyd. Chem. 6, 291(1951), J. C. Sowden: Carbohyd. Chem. Vol. I.132 (1962)). [Η. H. Baer: Carbohyd. Chem.Biochem. 24,67 (1969)], pósobením nitrome-tanu a metylátu sodného na L-xylózu připra-vil zmes sodných solí 1-deoxy-l-nitro-L-gu-litolu a 1-deoxy-l-nitro-L-iditolu, ktorú porozpuštění vo vodě deionizoval a získal 45až 50% výťažok 1-deoxy-l-nitro-L-gulitolua 1-deoxy-l-nitro-L-iditolu. Podlá nášho zis-tenia sodné soli 1-deoxy-l-nitro-L-gulitolua 1-deoxy-l-nitro-L-iditolu sa hydrolyzujúvodou na L-xylózu, čím sa sťažuje kryštali-zácia a znižuje výťažok 1-deoxy-l-nitro-L-gu-litolu a 1-deoxy-l-nitro-L-iditolu.The invention relates to a process for the preparation of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol. 1-deoxy-1-nitroalditols prepared by nitrorethane synthesis [J. C. Sowden, H. O. L. Fischer: J. Am. Chem. Soc. 67, 1713 (1945), J. C. Sowden: Adv. Carbohyd. Chem. 6, 291 (1951), J. C. Sowden: Carbohyd. Chem. Vol. I.132 (1962)). [Η. H. Baer: Carbohyd. Chem.Biochem. 24.67 (1969)], by the action of sodium nitrite and sodium methylate on L-xylose, a mixture of sodium salts of 1-deoxy-1-nitro-L-guenol and 1-deoxy-1-nitro-L-iditol was prepared which has been deionized by dissolution in water to yield 45 to 50% yield of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol. According to our determination of the sodium salt of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol, it is hydrolyzed to L-xylose, thereby making crystallization difficult and reducing the yield of 1-deoxy-1 -nitro-L-guolite and 1-deoxy-1-nitro-L-iditol.
Uvedené nevýhody v podstatné] miere od-straňuje spósob přípravy 1-deoxy-l-nitro-L--gulitolu a 1-deoxy-l-nitro-L-iditolu podlávynálezu, ktorého podstata spočívá v tom, žesa sodné soli 1-deoxy-l-nitro-L-gulitolu a 1--deoxy-l-nitro-L-iditolu před deionizáciourozpustia v zriedene] kyselině octovej. Roz-tok sa podrobí deionizácii cez vymieňač ka-tiónov a zahustí na sirup. Výhodou navrhovaného spósobu přípravy 1-deoxy-l-nitro-L-gulitolu a 1-deoxy-l-nitro--L-iditolu oproti doterajším postupom přípra-vy je, že předmětný spósob je hospodárnějšílebo dává až 87% výtažky 1-deoxy-l-nitro-L--gulitolu a 1-deoxy-l-nitro-L-iditolu. Příklad 1The above mentioned disadvantages are substantially hindered by the method of preparation of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol, which is based on the fact that the sodium salts of 1-deoxy- 1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol are dissolved in dilute acetic acid before deionization. The solution is deionized through a cation exchange and concentrated to a syrup. The advantage of the proposed method for the preparation of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol is that the present method is more economical or gives up to 87% yields of 1-deoxy-1-nitro-L-iditol. 1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol. Example 1
Zmes L-xylózy (300 g) sa mieša v sulfonač-nej banke, ktorá je opatřená chladičom,chlorkalciovým uzáverom s roztokom mety-látu sodného připraveného rozpuštěním(63 g) sodíka v (2700 ml) metylalkoholua s nitrometanom (1080 ml) pri 20 °C podobu 12 h. Vylúčené sodné soli 1-deoxy-l--nitro-L-gulitol a 1-deoxy-l-nitro-L-iditol saodfiltrujú, premyjú metylalkoholom (500 ml]a rozpustia v 10% kyselině octovej (4000 ml).Roztok sa deionizuje cez kolonu vymieňačakatiónov o rozmeroch s dížkou 100 cm a prie-merom 4 cm. Eluát z kolóny sa vákuom za-hustí a lyofilizuje. Získá sa 366 g zmesi1-deoxy-l-nitro-L-gulitol a 1-deoxy-l-nitro-L--iditol v 87,2 % výtažku.A mixture of L-xylose (300 g) was stirred in a sulfonation flask equipped with a condenser, a chlorine-stopper with a sodium methylate solution prepared by dissolving (63 g) sodium in (2700 ml) methanol and nitromethane (1080 ml) at 20 ° C. The precipitated sodium salts of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol are filtered, washed with methanol (500 ml) and dissolved in 10% acetic acid (4000). The solution is de-ionized through a column of 100 cm diameter and 4 cm diameter exchangers, and the column eluate is vacuum-dried and lyophilized to give 366 g of 1-deoxy-1-nitro-L-gulitol and 1 g. -deoxy-1-nitro-L-iditol in 87.2% yield.
Vynález má rozsiahle využitie pri príprave1-deoxy-l-nitro-L-gulitolu a 1-deoxy-l-nitro--L-iditolu, ktoré sú medziproduktami pri pří-pravě ťažko dostupných vzácných sacharidovL-gulózy a L-idózy. Tieto látky sa používajúpri studiu bichemických pochodov a v me-dicíně. 225577The present invention has extensive utility in the preparation of 1-deoxy-1-nitro-L-gulitol and 1-deoxy-1-nitro-L-iditol, which are intermediates in the preparation of scarcely available rare saccharide-L-gulose and L-idose. These substances are used in the study of bichemical processes and in medicine. 225577
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS721982A CS225577B1 (en) | 1982-10-11 | 1982-10-11 | Preparation of 1-deoxy-1-nitro-l-gulithol and 1-deoxy-1-nitro-6-iditol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS721982A CS225577B1 (en) | 1982-10-11 | 1982-10-11 | Preparation of 1-deoxy-1-nitro-l-gulithol and 1-deoxy-1-nitro-6-iditol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS225577B1 true CS225577B1 (en) | 1984-02-13 |
Family
ID=5420942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS721982A CS225577B1 (en) | 1982-10-11 | 1982-10-11 | Preparation of 1-deoxy-1-nitro-l-gulithol and 1-deoxy-1-nitro-6-iditol |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS225577B1 (en) |
-
1982
- 1982-10-11 CS CS721982A patent/CS225577B1/en unknown
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