(Diethylamino)sulfur trifluoride → (2,3,4-tri-O-acetyl)-L-fucopyranosyl fluoride

HRID 580831Notes

Reaction equation

HRID 580831 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][CH:6]1O)(=[O:3])[CH3:2].CCN(S(F)(F)[F:27])CC>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][CH:6]1[F:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10979132GlyTouCan:G58715BY

Product 1

HCID 21309973(2,3,4-tri-O-acetyl)-L-fucopyranosyl fluorideYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,3,4-Tri-O-acetyl)-L-fucopyranose (13.1 g) is dissolved in methylene chloride (100 ml), and thereto is added with stirring DAST (10.9 g) under ice-cooling, and the mixture is stirred for 4 hours under ice-cooling. The reaction mixture is poured into ice-water (200 g), and the mixture is separated. The organic layer is dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:4→1:2) to give (2,3,4-tri-O-acetyl)-L-fucopyranosyl fluoride (10.6 g) in the form of a mixture of α-anomer and β-anomer.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe mixture is separated
  4. customThe organic layer is dried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:4→1:2)

Sources & evidence

ORD record
ord-8c761c134c2b4cdcaaa7b8519cd78608
Source dataset
uspto-grants-1999_07
Patent number
US05919769

Reaction notes

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