Hydrofluoric Acid → alpha-D-galactosyl fluoride

HRID 231623

Reaction equation

HRID 231623 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])O.[FH:13]>>[C@H:11]1([F:13])[O:12][C@H:3]([CH2:2][OH:1])[C@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]1[OH:10]

Participants

3

Reactant 2

HCID 14917Hydrofluoric Acid2×HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 10921145alpha-D-galactosyl fluorideYield 98.9%

Procedure

In an apparatus and by the procedure according to Example 1, 1 g of D-galactose was reacted with 10 g of hydrogen fluoride, the mixture was left to stand for 1 hour at -30° to -40° C. and the hydrogen fluoride was then stripped out within 15 minutes by blowing in nitrogen. The working-up gave α-D-galactosyl fluoride (about 1 g) which was identified by elemental analysis, thin-layer chromatogram and 19F and 13C nuclear magnetic resonance spectra (cf. J. E. C. Barnett et al., Biochem. J. 105 (1967), page 669). Melting point: 130° (decomposition).

Workup

  1. waitthe mixture was left
  2. customwas then stripped out within 15 minutes

Sources & evidence

ORD record
ord-16776c047081431289aa1e48fce5fd59
Source dataset
uspto-grants-1989_07
Patent number
US04847372

Linked notes

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