Pyridine → 1,4-Anhydro-2-deoxy-D-erythro-pentitol 5-(Trifluoromethanesulfonate)

HRID 54808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54808
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]1[O:21][C@H:20]([CH2:22]O)[C@@H:18]([OH:19])[CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:22][C@H:20]1[O:21][CH2:16][CH2:17][C@@H:18]1[OH:19])(=[O:5])=[O:4]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1246571,2-Dideoxyribofuranose

Produkt 1

HCID 867503491,4-Anhydro-2-deoxy-D-erythro-pentitol 5-(Trifluoromethanesulfonate)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a -20° C. solution, under argon, of 8.4 ml of trifluoromethanesulfonic anhydride in 75 ml of methylene chloride is added, dropwise, a solution of 5.9 g of product from Example 268 and 4.05 ml of pyridine in 25 ml of methylene chloride. The temperature is maintained below -10° C. during the addition. The progress of the reaction is monitored by tic. The reaction is filtered and the filtrate concentrated in vacuo to an oily residue, The residue is purified by chromatography (silica gel: 50% ethyl acetate/hexane) to give 7.03 g of the desired product.

Aufarbeitung

  1. temperatureThe temperature is maintained below -10° C. during the addition
  2. filtrationThe reaction is filtered
  3. concentrationthe filtrate concentrated in vacuo to an oily residue
  4. customThe residue is purified by chromatography (silica gel: 50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9cf9b2e152cf4134b30a35eb7c1e4df0
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623081

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