Sulfuric Acid → alpha-L-glucopyranose

HRID 1706578Notes

Reaction equation

HRID 1706578 reaction equation
[N+]([CH2:4][C@H:5]([C@@H:7]([C@H:9]([C@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])[OH:6])([O-])=O.S(=O)(=O)(O)[OH:16].[OH-].[Ba+2].[OH-]>[OH-].[Na+].O>[OH:16][C@@H:4]1[O:12][C@@H:11]([CH2:13][OH:14])[C@H:9]([OH:10])[C@@H:7]([OH:8])[C@@H:5]1[OH:6]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6093286Barium hydroxideHCID 133883171-Deoxy-1-nitro-L-glucitol

Product 1

HCID 6971003alpha-L-glucopyranose

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1-Deoxy-1-nitro-L-glucitol (5.0 g.) was dissolved in 2 N sodium hydroxide (15 ml.) and the solution was immediately added dropwise to a stirred, cooled (ice-bath) solution of sulfuric acid (7.5 ml.) in water (9.0 ml.). The solution was then diluted with water (175 ml.) and neutralized to Congo Red with warm barium hydroxide solution. The precipitated barium sulfate was removed by centrifugation and the remaining sulfate was precipitated with a slight excess of barium acetate. The solution was then filtered through a pad of Celite® and the filtrate de-ionized by passage through a column containing 50 ml. of Dowex® 50W-X8 (H+) resin. The effluent and washings were evaporated under reduced pressure to a syrup which was diluted with a few drops of ethanol, warmed to 50°, seeded (seed crystals obtained from previous experiments) and allowed to crystallize. The resulting crystals were filtered with the aid of cold ethanol to give, after recrystallization, α-L-glucopyranose (2.4 g.), m.p. 146°-147°, [α]D -100°→-53.3° (24 hr.; c 2.15, water), compared to m.p. 146°-147°, [α]D -53° (at equilibrium; c 2.6, water). The filtrate containing L-glucose (t.l.c., n-propanol/ethyl acetate/water v/v 3:1:1) was retained for use in subsequent preparations of L-glucose.

Workup

  1. additionthe solution was immediately added dropwise to a stirred
  2. customThe precipitated barium sulfate was removed by centrifugation
  3. customthe remaining sulfate was precipitated with a slight excess of barium acetate
  4. filtrationThe solution was then filtered through a pad of Celite®
  5. additionthe filtrate de-ionized by passage through a column containing 50 ml
  6. customThe effluent and washings were evaporated under reduced pressure to a syrup which
  7. additionwas diluted with a few drops of ethanol
  8. temperaturewarmed to 50°
  9. custom(seed crystals obtained from previous experiments)
  10. customto crystallize
  11. filtrationThe resulting crystals were filtered with the aid of cold ethanol
  12. customto give
  13. customafter recrystallization, α-L-glucopyranose (2.4 g.), m.p. 146°-147°, [α]D -100°→-53.3° (24 hr.; c 2.15, water)
  14. additionThe filtrate containing L-glucose (t.l.c

Sources & evidence

ORD record
ord-2a4c97a260d94db3b959ba3db6c72e3b
Source dataset
uspto-grants-1980_06
Patent number
US04207413

Reaction notes

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