delta-Gluconolactone → (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

HRID 46186

Reaktionsgleichung

Reaktionsgleichung von HRID 46186
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11].[CH2:21]([Li])[CH2:22][CH2:23][CH3:24].[CH2:26]([OH:37])[C@H:27]1[O:33][C:31](=[O:32])[C@H:30]([OH:34])[C@@H:29]([OH:35])[C@@H:28]1[OH:36]>O1CCCC1>[CH2:21]([O:34][C@@H:30]1[C@@H:29]([O:35][CH2:21][C:22]2[CH:11]=[CH:10][CH:12]=[CH:24][CH:23]=2)[C@H:28]([O:36][CH2:21][C:22]2[CH:14]=[CH:13][CH:15]=[CH:24][CH:23]=2)[C@@H:27]([CH2:26][O:37][CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][CH:19]=2)[O:33][C:31]1([C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:19]=1)[OH:32])[C:22]1[CH:18]=[CH:16][CH:17]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 7027delta-Gluconolactone2×HCID 67153939(5-Bromo-2-chlorobenzyloxy)triisopropylsilane2×HCID 178418339Butyllithium

Produkt 1

HCID 67287055(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (5-Bromo-2-chlorobenzyloxy)triisopropylsilane (compound 4, 97 g, 257 mmol) from Step 3 in tetrahydrofuran (1 L) at −78° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (2.5 M in hexanes, 103 mL, 257 mmol), and the mixture was stirred for 1.5 h at the same temperature. Then a solution of 2,3,4,6-tetra-O-benzyl-D-glucopyranone (compound 2, 106 g, 198 mmol) from Step 1 in tetrahydrofuran (500 mL) was added dropwise, and the mixture was stirred for 3 h at the same temperature. The reaction mixture was quenched by addition of saturated ammonium chloride solution. After complete addition, the solution was gradually raised to room temperature. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellow oil which was used without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred for 3 h at the same temperature
  2. customThe reaction mixture was quenched by addition of saturated ammonium chloride solution
  3. additionAfter complete addition
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a780a61119ba441c9529ed88dfc75f77
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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