aldehydo-D-Xylose → HCID 178478778, Verbindung

HRID 81332

Reaktionsgleichung

Reaktionsgleichung von HRID 81332
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].N[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([NH:28][C:29]([C:31]2[C:36]([NH2:37])=[N:35][C:34]([NH2:38])=[C:33]([Cl:39])[N:32]=2)=[O:30])=[NH:27])=[CH:17][CH:16]=1.[C:40]([BH3-])#[N:41].[Na+]>CO>[ClH:39].[ClH:39].[OH:4][C@@H:3]([C@H:5]([OH:6])[C@H:7]([OH:8])[CH2:9][OH:10])[CH2:2][N:41]([CH2:40][C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]([OH:6])[CH2:3][OH:4])[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([NH:28][C:29]([C:31]2[C:36]([NH2:37])=[N:35][C:34]([NH2:38])=[C:33]([Cl:39])[N:32]=2)=[O:30])=[NH:27])=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 644160aldehydo-D-XyloseHCID 5003444Sodium cyanoborohydrideHCID 178512152HCID 178512152, Verbindung

Produkt 1

HCID 178478778HCID 178478778, VerbindungAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

D-(+)-xylose (0.35 g, 2.6 mmol) was added to a solution of hydrochloride 4 (0.3 g, 0.65 mmol) in methanol (20 mL) and the mixture was stirred for 20 min at room temperature. Then the solution was cooled to −78° C. and sodium cyanoborohydride (0.17 g, 2.6 mmol) was added. The reaction mixture was stirred at −78° C. for 2 h and at room temperature for 4 d. After this time, the solvent was removed under reduced pressure and the residue was washed with water. The formed yellow solid was isolated and dried under vacuum. Then the residue was re-dissolved in 5% HCl and the solvent was removed at reduced pressure. The obtained compound was dissolved in water containing 0.1% TFA and purified by preparative HPLC (C 18 Luna column from Phenomenex 250×21.2 mm, 5μ, isocratic method, water/acetonitrile=80%:20%). The fractions containing the target compound were combined and the solvent was removed under reduced pressure. The residue was dissolved in 5% HCl and solvent was removed under reduced pressure (twice). The resulting yellow powder was dissolved in water and the solution was lyophylized to give 34 mg (7%) of compound 23 as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 1.64 (br s., 4H), 2.62 (m, 2H), 3.30 (m, 4H), 3.35-3.70 (m, 13H), 4.23 (m, 2H), 4.47 (m, 2H), 6.95 (d, 2H), 7.15 (d, 2H). m/z (APCI)=689 [C28H45ClN8O10+H]+. [α]D25=−16.1° (c=0.5, MeOH).

Aufarbeitung

  1. temperatureThen the solution was cooled to −78° C.
  2. stirringThe reaction mixture was stirred at −78° C. for 2 h and at room temperature for 4 d
  3. customAfter this time, the solvent was removed under reduced pressure
  4. washthe residue was washed with water
  5. customThe formed yellow solid was isolated
  6. customdried under vacuum
  7. dissolutionThen the residue was re-dissolved in 5% HCl
  8. customthe solvent was removed at reduced pressure
  9. dissolutionThe obtained compound was dissolved in water containing 0.1% TFA
  10. custompurified by preparative HPLC (C 18 Luna column from Phenomenex 250×21.2 mm, 5μ, isocratic method, water/acetonitrile=80%:20%)
  11. additionThe fractions containing the target compound
  12. customthe solvent was removed under reduced pressure
  13. dissolutionThe residue was dissolved in 5% HCl
  14. customsolvent was removed under reduced pressure (twice)
  15. dissolutionThe resulting yellow powder was dissolved in water

Quellen und Nachweise

ORD-Eintrag
ord-eb41a332e2e24f28b2e765f175733482
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846688B2

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