Tetramethyltin → 1,6-anhydro-3,4-dideoxy-3-methyl-beta-D-glycero-hex-3-enopyranos-2-ulose

HRID 1769236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1769236
C[Sn](C)(C)C.[CH3:6]N1CCCC1=O.I[C:14]1[C:15](=[O:22])[C@@H:16]2[O:21][CH2:20][C@H:18]([CH:19]=1)[O:17]2.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu]I.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C>[CH3:6][C:14]1[C:15](=[O:22])[C@@H:16]2[O:21][CH2:20][C@H:18]([CH:19]=1)[O:17]2

Komponenten

8

Edukt 4

HCID 11661TetramethyltinHCID 11773TriphenylarsineHCID 13387N-methyl-2-pyrrolidoneHCID 80272516,8-Dioxabicyclo[3.2.1]oct-2-en-4-one, 3-iodo-, (1S,5R)-

Produkt 1

HCID 701307781,6-anhydro-3,4-dideoxy-3-methyl-beta-D-glycero-hex-3-enopyranos-2-ulose

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 498840Bis(benzonitrile)palladium chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5.3 g of tetramethyltin was added to 20 ml of a dry N-methylpyrrolidinone solution containing a mixture comprising 5 g of 1,6-anhydro-3,4-dideoxy-3-iodo-β-D-glycero-hex-3-enopyranos-2-ulose, 0.4 g of copper(I) iodide, 0.6 g of triphenylarsine and 0.4 g of dichlorobis(benzonitrile)palladium(II) under an inert atmosphere of nitrogen gas. The mixture was stirred at 80° C. for 4 hours. Then, 200 ml of ethyl acetate was added thereto, and the mixture was washed three times with 100 ml of a 10% potassium fluoride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained syrup product was purified by silica gel column chromatography (ethyl acetate: hexane=1:3) and then distilled under reduced pressure to obtain 1.61 g of the desired product (Intermediate No. 2) as a colorless transparent liquid. The NMR analytical data of this product are as follows.

Aufarbeitung

  1. washthe mixture was washed three times with 100 ml of a 10% potassium fluoride aqueous solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained syrup product was purified by silica gel column chromatography (ethyl acetate: hexane=1:3)
  5. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c715a54ebc0342aeb4d04ff8f7b30de9
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05380834

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