CS274098B1 - Method of n-phenyl-d-manosilamine preparation from mixture of d-glucose and d-mannose - Google Patents
Method of n-phenyl-d-manosilamine preparation from mixture of d-glucose and d-mannose Download PDFInfo
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- CS274098B1 CS274098B1 CS630089A CS630089A CS274098B1 CS 274098 B1 CS274098 B1 CS 274098B1 CS 630089 A CS630089 A CS 630089A CS 630089 A CS630089 A CS 630089A CS 274098 B1 CS274098 B1 CS 274098B1
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- mannose
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- aniline
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 title 1
- GZCGUPFRVQAUEE-KVTDHHQDSA-N aldehydo-D-mannose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KVTDHHQDSA-N 0.000 title 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 16
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 5
- 230000008025 crystallization Effects 0.000 claims description 4
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 229960001031 glucose Drugs 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000001312 aldohexoses Chemical class 0.000 description 7
- 150000001323 aldoses Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- OSNSWKAZFASRNG-WNFIKIDCSA-N (2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;hydrate Chemical compound O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O OSNSWKAZFASRNG-WNFIKIDCSA-N 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001304 aldoheptoses Chemical class 0.000 description 1
- 150000001320 aldopentoses Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 150000002671 lyxoses Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
Description
Vynález sa týká sposobu přípravy N-fenyl-D-manozylaminu zo zmesi D-manózy a □-glukózy.The present invention relates to a process for the preparation of N-phenyl-D-manozylamine from a mixture of D-mannose and □-glucose.
V mnohých pripadoch N-arylglykozylmíny aldóz sú dobré kryštalizujúce zlúčeniny / G. P. Cllis, 3. Honeyman: Advan. Carbohyd. Chem. 10, 95 (1955)J7 a ich rozna kryštalizačná schopnost sa využívá aj na vzájomná rozdelenie aldóz, resp. aldóz od ketóz.In many cases, the N-arylglycosylmines of aldoses are good crystallizing compounds / G. P. Cllis, 3. Honeyman: Advan. Carbohyd. Chem. 10, 95 (1955) J7 and their distinct crystallization ability is also used for the distribution of aldoses, respectively. aldoses from ketoses.
Zo všetkých aldopentóz, aldohexóz a aldoheptóz vykazujú velmi dobrú kryštalizačnú schopηο3Ϊ N-fenylglykozylaminy ribózy, lyxózy, manózy a manoheptózy. Ak sa tieto aldózy nachádzajú v zmesiach aldóz resp. ketóz v dostatočných množstvách, možno ich izoloval vo formě krystalických N-fenylglykozylaminov ribózy /7R· L· Whistler, W. 3. BeMillers Methods Carbohyd. Chem., Vol. X, p. 79, Asademic Press, New York - London 1962; V. Bilik, 3. Caplovič: Chem. Zvěsti 27, 547 (1973)J, lyxózy Γ V. Bilik, 3. Caplovič:Of all aldopentoses, aldohexoses and aldoheptoses, ribose, lyxose, mannose, and manoheptosis have a very good crystallization capacity. If these aldoses are present in mixtures of aldoses resp. ketosis in sufficient quantities, they may be isolated as a crystalline N-ribose fenylglykozylaminov / 7 · R · L Whistler, W 3 BeMillers Methods Carbohyd. Chem., Vol. X, p. 79, Asademic Press, New York-London, 1962; V. Bilik, 3. Caplovich: Chem. Rumors 27, 547 (1973) J, Lyxoses Γ V. Bilik, 3rd Caplovich:
Chem. Zvěsti 27, 547 (1973)J, manózy /T. Fujita, T, Sáto; Bull, Chem. Soc, 3apan 33,Chem. Rumors 27, 547 (1973) J, Mannose / T. Fujita, T, Sato; Bull. Chem. Sap, 3apan 33,
353 (1960)/ V. Bilik, !<. Tlhlárik: Chem. Zvěsti 28, 106 (1974)J, manoheptózy /7 V. Bilik, L. Petruš: Chem. Zvěsti 30, 359 (1976)_/. Tieto vlastnosti N-fenylglykozylaminov uvedených aldóz boli využité na ich izoláclu od odpovedajúcich C(2) -epímárnych akdóz. Na izoláciu L-arabinózy z hydrolyzátu hemicelulóz, alebo izoláciu arabinózy od xylózy £ M. Bilik. A. Kramář: Chem. Zvěsti 33, 641 (1979)J7, připadne izoláciu353 (1960) / V. Bilik, J. <. Chem. Rumors 28, 106 (1974) J, Manoheptoses / 7 V. Bilik, L. Petruš: Chem. Rumors 30, 359 (1976). These N-phenylglycosylamine properties of said aldoses have been utilized to isolate them from the corresponding C (2) -immediate acdoses. To isolate L-arabinose from a hemicellulose hydrolyzate, or isolate arabinose from xylose. A. Kramar: Chem. Rumors 33, 641 (1979) J7 may be isolated
D-glukózy z hydrolyzátu sacharózy a D-manózy z hydrolyzétov manánov /3. Weygand, W. Perkov, P. Kuhner: Ber. 34, 594 (1951)_7 sa osvědčili dobré kryštalizujúce 4-nitrofenyl-N-glykozylaminy erabinózy, glukózy a manózy. V žiadnom případe sa však nedosahuje kvantitativná výíažnosl aldózy vo formě dobré kryštalizujúceho N-fenyl- resp. 4-nitrofenyl-N-glykozylaminu.D-glucose from sucrose hydrolyzate and D-mannose from mannan hydrolyzates / 3. Weygand, W. Perkov, P. Kuhner, Ber. 34, 594 (1951) 7 have proven to be good crystallizing 4-nitrophenyl-N-glycosylamines of erabinose, glucose and mannose. However, the quantitative yield of the aldose in the form of a good crystallizing N-phenyl- and / or N-phenyl is in no way achieved. 4-nitrophenyl-N-glycosylamine.
Uvedenu nevýhodu v podstatnej miere odstraňuje sposob pripravy N-fenyl-D-manozylaminu zo zmesi D-glukózy a D-manózy, ktorého podstata spočivá v tom, že na zmes D-manózy a D-glukózy v mólovom pomere 1 : 1 až 2 rozpustenej v zmesi metanolu a etanolu s obsahom 5 až 10 obj. % vody sa pósobí anilinom v množstve 50 až 80 % teoretického množstva počitaného na aldohexózy a vzniklý N-fenyl-D-manozylaminu sa izoluje kryštalizáciou.This disadvantage is substantially eliminated by the process of preparing N-phenyl-D-mannose amine from a mixture of D-glucose and D-mannose, which consists in the fact that the molar ratio of D-mannose and D-glucose in a molar ratio of 1: 1 to 2 is dissolved. in a mixture of methanol and ethanol containing 5 to 10 vol. % of water is treated with aniline in an amount of 50 to 80% of the theoretical amount calculated for aldohexoses, and the resulting N-phenyl-D-manozylamine is isolated by crystallization.
Výhodou navrhovaného spósobu pripravy N-fenyl-D-manozylaminu zmesi D-manózy a D-glukózy je, že pri použiti iba 50 až 80% teoretického množstva anilinu na aldohexózy sa ziska 89 až 100% výlažok D-manózy vo formě N-fenyl-D-manozylaminu. Ďalšou výhodou je, že zpBsob izolácie D-manózy Je nenáročný na technologické zariadenia a potřebné chemikálie .An advantage of the proposed process for the preparation of N-phenyl-D-manozylamine with a mixture of D-mannose and D-glucose is that using only 50-80% of the theoretical amount of aniline per aldohexose yields 89-100% of D-mannose as N-phenyl- D-manozylaminu. A further advantage is that the process of isolating D-mannose is unpretentious for technological equipment and the necessary chemicals.
Přiklad 1Example 1
Zmesi 198 g (1 mol) mohohydrátu D-glukózy, 20 ml 6% vodného roztoku tetrahydrótu heptamolybdónanu hexaamonného a 2 ml 98 hmot. % kyseliny octovej sa zahrieva pri teplote 95 až 100 °C počas 3 h. Do reakčnej zmesi vychladnutej na 60 až 70 °C sa za miešania přidá 100 ml metanolu a potom 100 ml 96 hmot. % denaturovanóho etanolu. Roztok sa nechá krystalizoval pri teplote 20 až 23 °C počas 48 h. Kryštalická D-glukóza 69 g (0,35 mol) sa odfiltruje a premyje malým množstvom zmesi alkoholov metanolu a etanolu v objemovom pomere 1 : 1. Filtrát sa upravi rovnakou zmesou metanolu a 96 hmot. % etanolu na 400 ml objem a přidá sa 29,6 ml (0,33 mol) anilinu (mólový poměr aldohexóz ku anilinu je 1 : 0,5). Po 5 h.stétia roztoku sa odfiltruje 57,4 g kryštalického N-fenyl-D-manozylaminu. Týmto sposobom sa ziska 22,5% výlažok D-manózy vo formě N-fenyl/D-manozylaminu počítané na východisková D-glukózu.Mixtures 198 g (1 mol) of D-glucose monohydrate, 20 ml of a 6% aqueous solution of hexa-ammonium heptamolybdate tetrahydrate and 2 ml of 98 wt. % acetic acid is heated at 95-100 ° C for 3 h. To the reaction mixture cooled to 60-70 ° C, 100 ml of methanol and then 100 ml of 96 wt. % denatured ethanol. The solution was left to crystallize at 20-23 ° C for 48 h. Crystalline D-glucose 69 g (0.35 mol) was filtered off and washed with a small amount of a 1: 1 v / v mixture of methanol and ethanol. % ethanol to 400 ml volume and 29.6 ml (0.33 mol) of aniline (molar ratio of aldohexoses to aniline of 1: 0.5) is added. After 5 h of solution, 57.4 g of crystalline N-phenyl-D-manozylamine are filtered off. In this way, 22.5% yields of D-mannose are obtained in the form of N-phenyl / D-manozylamine calculated on the starting D-glucose.
Přiklad 2Example 2
Postupuje sa ako v přiklade 1 s tým rozdielom, že sa přidá 35,5 ml (0,39 mol) anilinu (mólový poměr aldohexóz ku anilinu Je 1 : 0,6), čim sa ziska 24,4% výlažok D-manozy vo formě N-fenyl-D-manozylaminu počítané na východiskové D-glukózu.The procedure is as in Example 1 except that 35.5 ml (0.39 mol) of aniline (molar ratio of aldohexoses to aniline is 1: 0.6) is added, yielding 24.4% of the D-mannose yield in the the N-phenyl-D-manozylamine form calculated on the starting D-glucose.
Přiklad 3Example 3
Postupuje sa ako v přiklade 1 s tým rozdielom, že sa přidá 41,9 ml (0,46 mol) anilinu (mólový poměr aldohexóz ku anilínu je 1 : 0,7), čim sa ziska 25,0% výlažok D-manozyThe procedure is as in Example 1 except that 41.9 ml (0.46 mol) of aniline (mole ratio of aldohexoses to aniline is 1: 0.7) is added to obtain 25.0% of D-mannose yield.
CG 274000 Dl vo formo N-fenyl-D-manozylaminu počítané na východiskoví! D-glukózu.CG 274000 D1 in the form of N-phenyl-D-manozylamine calculated on the starting! D-glucose.
Přiklad 4Example 4
Postupuje sa ako v přiklade 1 s tým rozdielom, že ee přidá 47,4 ml (0,02 mol) anilinu (mólový poměr aldohexóz ku anilinu je 1 j 0,8), čim ea zieka 25,1% výfažok D-manózy vo forma N-fenyl-D-manozylominu počítané na východiekovú D-glukózu.The procedure is as in Example 1 except that 47.4 ml (0.02 mol) of aniline (the molar ratio of aldohexoses to aniline is 1: 0.8) is added to yield a 25.1% D-mannose extract in the N-phenyl-D-mannosylomine form calculated on the D-glucose starting material.
Přiklad 5Example 5
Zmes 14,85 g (75 mmol) monohydrátu D-glukózy, 13,5 g (75 mmol) D-manózy, 6 ml vody o 0,5 ml 98 hmot. % kyseliny octovej aa zahraje na 95 až 100 °C. Po vychladnuti roztoku na teplotu 60 až 70 °C sa za miešania přidá 40 ml metanolu, potom 40 ml 96 hmot, % etanolu, nakoniec 11 ml (0,12 mol) anilínu (mólový poměr aldohexóz ku anilínu Je 1 : 0,8) e roztok sa nechá, stáf pri teplote 20 až 23 °C počas 5 h. Odfiltrováním sa získá 19,1 g krystalického N-fenyl-D-manozylamínu, čo představuje 99,7% výfažok východiekovej D-manózy vo formo N-fonyl-O-manozylaminu.A mixture of 14.85 g (75 mmol) of D-glucose monohydrate, 13.5 g (75 mmol) of D-mannose, 6 ml of water with 0.5 ml of 98 wt. % acetic acid and heated to 95-100 ° C. After cooling the solution to 60-70 [deg.] C., 40 ml of methanol, then 40 ml of 96% by weight of ethanol are added, with stirring, and finally 11 ml (0.12 mol) of aniline (molar ratio of aldohexoses to aniline is 1: 0.8). The solution is allowed to stand at 20 to 23 ° C for 5 h. Filtration gave 19.1 g of crystalline N-phenyl-D-manozylamine, which is 99.7% yield of the starting D-mannose in the form of N-phonyl-O-manozylamine.
Přiklad 6Example 6
Postupuje sa ako v přiklade 5 s tým rozdielom, že ea pripravi zmes 19,8 g (100 mmol) monohydrátu D-glukózy, 9,0 g (50 mmol) D-manózy, 5,5 ml vody a 0,5 ml 98 hmot. % kyseliny octovej. Odfiltrováním sa zieka 12,55 g kryátolického N-fenyl-D-menozylaminu, čo představuje 98,3% výfažok východiakovej D-manózy vo formě N-fenyl-D-manozylaminu.The procedure was as in Example 5 except that e prepared a mixture of 19.8 g (100 mmol) D-glucose monohydrate, 9.0 g (50 mmol) D-mannose, 5.5 ml water and 0.5 ml 98. wt. % acetic acid. Filtration yielded 12.55 g of crystalline N-phenyl-D-menozylamine, which represents 98.3% yield of the starting D-mannose as N-phenyl-D-manozylamine.
Porovnanlo účinku zniženóho pridovku anilínu o doteraz používaným nadbytočným množstvom anilinu počítaným no aldohoxózy ukazuje noeledovný přiklad;Comparing the effect of the reduced aniline additive by the excess amount of aniline used hitherto calculated by no aldohoxosis shows a noeled example;
Přiklad 7Example 7
Postupuje so ako v příklade 1 s tým rozdielom, žo ea přidá 65,6 ml (0,72 mol) anilinu (mólový poměr aldohoxóz ku anilínu je 1 : 1,1), čim sa zieka 25,3% výfažok ϋ-manózy vo forma N-fenyl-D-manozylaminu počítaná na východisková D-glukózu.The procedure is as in Example 1 except that 65.6 ml (0.72 mol) of aniline (molar ratio of aldohoxoses to aniline is 1: 1.1) is added, yielding a 25.3% ϋ-mannose extract in the N-phenyl-D-manozylamine form calculated on the starting D-glucose.
Porovnanie účinku izolécie D-manózy vo formo N-fonyl-D-manozylaminu o izoláciou D-manózy vo formo fenylhydrazónu D-manózy, ktorá Jo osvědčenou gravimetrickou metódou stanovenia D-manózy, ukazuje naolodovný přiklad:A comparison of the effect of isolation of D-mannose in the formo N-phonyl-D-manozylamine with the isolation of D-mannose in the formo phenylhydrazone of D-mannose, which is a proven gravimetric method for the determination of D-mannose, shows a lead example:
Přiklad OExample O
Postupuje sa ako je uvedené v přiklade 1 o tým rozdielom, že po odkryštalizovanl D-glukózy o úpravo filtrátu alkoholmi na 400 ml objem ea k filtrátu přidá 200 ml vody a 70,5 ml (0,72 mol) fenylhydrazinu (mólový poměr aldohoxóz ku fonylhydrazinu Jo 1 : 1,1). Po 20 h. stánia roztoku sa 68,0 g kryštalického fenylhydrazónu D-rtanózy odfiltruje. Týmto spÓsobom so zieka 25,2% výfažok D-msnózy vo formo fenylhydrazónu D-manózy.The procedure is as described in Example 1, except that after the D-glucose has been crystallized to adjust the filtrate to 400 ml by volume of alcohol, 200 ml of water and 70.5 ml (0.72 mol) of phenylhydrazine (molar ratio of aldohoxoses to phonylhydrazine Jo 1: 1.1). After 20 h. After standing the solution, 68.0 g of crystalline phenylhydrazone D-methanose are filtered off. This yields a 25.2% yield of D-mannose in the form of phenylhydrazone D-mannose.
Vynález može nájsf použitie pri přípravo D-manózy, ktorá má .využitie v organickej chómii a biochómii.The invention can be used in the preparation of D-mannose which has utility in organic chemistry and biochemistry.
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| CS630089A CS274098B1 (en) | 1989-11-07 | 1989-11-07 | Method of n-phenyl-d-manosilamine preparation from mixture of d-glucose and d-mannose |
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| CS630089A CS274098B1 (en) | 1989-11-07 | 1989-11-07 | Method of n-phenyl-d-manosilamine preparation from mixture of d-glucose and d-mannose |
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