SU248671A1 - METHOD OF OBTAINING DEZOKSIGLI'KOKOPHOSPHONISTYKhKYGT th ..,:. ::: o iazchI •• '' '•' '' •,., ... :: v., 'Nv: -: x; i!' ; 4ecKS '; * - - Google Patents
METHOD OF OBTAINING DEZOKSIGLI'KOKOPHOSPHONISTYKhKYGT th ..,:. ::: o iazchI •• '' '•' '' •,., ... :: v., 'Nv: -: x; i!' ; 4ecKS '; * -Info
- Publication number
- SU248671A1 SU248671A1 SU1266570A SU1266570A SU248671A1 SU 248671 A1 SU248671 A1 SU 248671A1 SU 1266570 A SU1266570 A SU 1266570A SU 1266570 A SU1266570 A SU 1266570A SU 248671 A1 SU248671 A1 SU 248671A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- kokophosphonistykhkygt
- iazchi
- dezoksigli
- 4ecks
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 3
- 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 description 3
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 3
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 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 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 carbohydrate phosphates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Description
Изобретение относитс к способу получеии фосфорсодержащих производных углеводов, в состав которых входит фосфоругле.родна св зь.This invention relates to a process for the preparation of phosphorus-containing derivatives of carbohydrates, which include a phospho-rounder bond.
Эти соединени как аналоги природных фосфатов углеводов могут быть использованы дл регулировани процессов л изнеде тельиости организмов.These compounds, as analogues of natural carbohydrate phosphates, can be used to regulate the processes of the waste of organisms.
Известен способ получени дезоксигликофосфонистых кислот взаимодействием 1,6-аигидросахара , например левоглюкозана, с фосфорноватистой кислотой и ее натриевой солью при сплавлении реагентов при 85-90°С.A known method for the preparation of deoxyglycophosphonic acids by the interaction of 1,6-aigid sugar, for example, levoglucosane, with hypophosphorous acid and its sodium salt during fusion of the reagents at 85-90 ° C.
Дл использовани более легко доступных исходных .веществ и повышени чистоты и выхода конечного продукта предлагаетс в качестве исходного углевода использовать монозу , например глюкозу, рибозу, и процесс ведут с азетропной отгонкой воды при нагревании до 80-85°С.To use more readily available starting materials and to increase the purity and yield of the final product, it is proposed to use monose, such as glucose, ribose, as the starting carbohydrate, and the process is carried out with azetropic distillation of water when heated to 80-85 ° C.
Строение получаемых соединений доказываетс окислением йодной кислотой.The structure of the compounds obtained is proved by the oxidation with iodic acid.
Пример 1. 6-Дезокси-6-глюкофосфониста кислота.Example 1. 6-deoxy-6-glufosfonista acid.
В приборе Дина - Старка нагревают 10 г глюкозы, 8 г фосфорноватистой кислоты и 40 мл бензола в течение 45 мин при температуре кипени бензола. За это врем из реакционной среды отгон етс 1 мл воды. Затем реакционную смесь выдерживают при 80-85°С In a Dean-Stark apparatus, 10 g of glucose, 8 g of hypophosphorous acid and 40 ml of benzene are heated for 45 minutes at the boiling point of benzene. During this time, 1 ml of water is distilled off from the reaction medium. Then the reaction mixture is maintained at 80-85 ° C
.лЕ.le
;2; 2
в течение 6 час, технический продукт выдел ют из реакционной среды переосаледением эфиром из метанола. После хроматографической очистки технического продукта на колонке с целлюлозой в системе изопропанол : аммиак : вода 7:1:2 выход 6-дезокси-6-глюкофосфонистой кислоты 35%. Rf 0,37 (система изопропанол : аммиак : .вода 7:1:1).within 6 hours, the technical product was separated from the reaction medium by recalculating ether from methanol. After chromatographic purification of a technical product on a column with cellulose in the system, isopropanol: ammonia: water 7: 1: 2, yield of 6-deoxy-6-glucophosphonic acid 35%. Rf 0.37 (system isopropanol: ammonia: water 7: 1: 1).
Найдено, %: С 29,35; 29,15; Н 6,55; 6,64; Р 12,02; 12,21.Found,%: C 29.35; 29.15; H 6.55; 6.64; P 12.02; 12.21.
Вычислено, %: С 29,4; Н 6,54; Р 12,6.Calculated,%: C 29.4; H 6.54; R 12.6.
П Р и м ер 2. В приборе Дина - Старка нагревают 10 г рибозы, 7 г фосфорноватистой кислоты и 40 мл бензола в течение 25 мин при температуре кипени бензола. За это врем из реакционной среды отгон етс 0,9 мл воды. Затем реакционную смесь выдерживают при 80-85°С в течение 6 час. Технический продукг выдел ют из реакционной среды переохлаждением эфиром из метанола. После хроматографической очистки технического продукта иа колонке с целлюлозой в системе изопропанол : аммиак : вода 7:1:2 выход 5-дезокси5-рибофосфонистой кислоты составл ет 28%. Rf 0,4 (система изопропанол : аммиак : вода 7: 1 :2). 34A and R 2. In a Dean-Stark device, 10 g of ribose, 7 g of hypophosphorous acid and 40 ml of benzene are heated for 25 minutes at the boiling point of benzene. During this time, 0.9 ml of water is distilled off from the reaction medium. Then the reaction mixture is maintained at 80-85 ° C for 6 hours. Technical product was separated from the reaction medium by supercooling with ether from methanol. After chromatographic purification of a technical product with a cellulose column in the isopropanol: ammonia: water 7: 1: 2 system, the yield of 5-deoxy-ribophosphonic acid is 28%. Rf 0.4 (system isopropanol: ammonia: water 7: 1: 2). 34
Предмет изобретени ни более легко доступных исходных веществThe subject matter of the invention is no more readily available starting materials.
Способ получени дезоксигликофосфонистых дукта, в качестве исходного углевода исполькислот на основе взаимодействи углеводов с зуют монозу, например глюкозу, .рибозу, и профосфорноватистой кислотой при нагревании, 5 цесс ведут с азеотропной отгонкой воды при отличающийс тем, что, с целью использова- нагревании до 80-85°G,The method for producing deoxy glycophosphonous duct, as a starting carbohydrate based on carbohydrate interactions, is monosized, for example, glucose, ribose, and hypophosphorous acid, when heated, 5 cess is azeotropic distilling water with, in order to use, to heat up to 80 -85 ° G,
2486 2486
и повышени чистоты и выхода конечного проand increasing the purity and yield of the final product.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU248671A1 true SU248671A1 (en) |
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