Ethyl Acetate → D-(+)-Glucal

HRID 877870

Reaktionsgleichung

Reaktionsgleichung von HRID 877870
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][CH:7]=[CH:6]1)(=O)C.C[O-].[Na+].CCOC(C)=O>CO>[O:8]1[C@H:9]([CH2:15][OH:16])[C@@H:10]([OH:11])[C@H:5]([OH:4])[CH:6]=[CH:7]1

Komponenten

5

Edukt 3

HCID 8857Ethyl Acetate2×HCID 688303Tri-O-acetyl-D-glucalHCID 10942334Sodium Methoxide

Produkt 1

HCID 2734736D-(+)-Glucal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The Tri-O-Acetyl-D-Glucal [SM-A](100 g, 367 mmol) is dissolved in dry MeOH [1.5 L], and then NaOMe (110 mmol, 5.95 g) is added into reaction mixture. Within about 20 minutes, TLC (40% EtOAc/60% hexanes & 100% EtOAc) confirmed de-acetylated glucal. The reaction is quenched with 50WX4 cation exchange resin until pH is near 7.0 by pH strip paper. The mixture is filtered and evaporated to dryness under vacuum to yield syrupy glucal intermediate IntA1(59 g). Theoretical yield 100 g×(146/272) 53.7 g TLC IntA1Rf=0.1, SiO2, 100% Ethyl Acetate

Aufarbeitung

  1. customThe reaction is quenched with 50WX4 cation exchange resin until pH
  2. filtrationThe mixture is filtered
  3. customevaporated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a34bf769c1bc49bcba050160bf95bac6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987430B2

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