Hydrofluoric Acid → Glucosyl fluoride

HRID 231622Notes

Reaction equation

HRID 231622 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]>>[CH: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

4

Reactant 3

HCID 14917Hydrofluoric AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178506046HCID 178506046, compound

Product 1

HCID 150967Glucosyl fluorideYield 94%

Procedure

In a distillation flask of polytetrafluoroethylene, a solution of 10 g of glucose in 100 g of hydrogen fluoride, prepared analogously to Example 1, was distilled under reduced pressure at an internal temperature of -30° C. The pressure was regulated between 100 and 130 mbar in such a way that steady distillation took place. After 2.5 hours, the residual HF content in the bottoms from the distillation was then only 5 g. The distillation was terminated, and the residue worked up in accordance with Example 1. 9.5 g of glucosyl fluoride were obtained.

Workup

  1. distillationwas distilled under reduced pressure at an internal temperature of -30° C
  2. distillationthat steady distillation
  3. distillationthe residual HF content in the bottoms from the distillation
  4. distillationThe distillation
  5. customwas terminated

Sources & evidence

ORD record
ord-42ae6068496a424696c1e24222fbf362
Source dataset
uspto-grants-1989_07
Patent number
US04847372

Reaction notes

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