Reaktion #74486

ord-b31e5f351ac54974a00c1d8451aa3bc6

Reaktionsgleichung

CCOc1ccc(Cc2cc([C@@H]3O[C@@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)ccc2Cl)nn1
(2S,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((6-ethoxypyridazin-3-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate
C[O-].[Na+]
NaOMe
→
CCOc1ccc(Cc2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)nn1
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((6-ethoxypyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Edukte

—
( H )
CCOc1ccc(Cc2cc([C@@H]3O[C@@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)ccc2Cl)nn1
(2S,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((6-ethoxypyridazin-3-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate
C[O-].[Na+]
NaOMe

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered
  2. 2
    Waschenthe resin was washed with MeOH
  3. 3
    Einengenthe combined filtrate and washings were concentrated as pale yellow solid

Vorschrift

To a solution of (2S,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((6-ethoxypyridazin-3-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (74 mg, 0.13 mmol) in MeOH (3 mL) was added NaOMe (0.2 mL), and the mixture was stirred for 1 h at room temperature. The mixture was neutralized with Amberlite IR-120 (H) resin, and filtered, the resin was washed with MeOH, and the combined filtrate and washings were concentrated as pale yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541380B2uspto-grants-2013_09