Sodium Methoxide → benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside

HRID 1948830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948830
[N:1]([C@H:4]1[C@@H:17]([O:18]C(=O)C(C)(C)C)[C@H:16]([F:25])[C@@H:15]([CH2:26][O:27]C(=O)C(C)(C)C)[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+:2]=[N-:3].C[O-].[Na+]>CO>[N:1]([C@H:4]1[C@@H:17]([OH:18])[C@H:16]([F:25])[C@@H:15]([CH2:26][OH:27])[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[N+:2]=[N-:3]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 86600947Benzyl 2-azido-2,4-dideoxy-4-fluoro-3,6-di-O-pivaloyl-beta-D-mannopyranoside

Produkt 1

HCID 86600946benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Compound (22) (180 mg, 0.387 mmol) was dissolved in methanol (8 ml), sodium methoxide (922 mg, 9.67 mmols) was added to the solution, and the mixture was reacted with stirring at 40° C. TLC revealed 4.5 hours later that the reaction mixture collected into a spot, and the mixture was neutralized with a cation-exchange resin IR-120(+), followed by filtration and concentration. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), giving Compound (23) (in an amount of 105.3 mg, 91.6% in yield).

Aufarbeitung

  1. customthe mixture was reacted
  2. customcollected into a spot
  3. filtrationfollowed by filtration and concentration
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4f94f06c38f7497bb76806e0539e2379
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399656B2

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