4-Toluenesulfonyl chloride → HCID 14214839, compound

HRID 1362774Notes

Reaction equation

HRID 1362774 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])[OH:4].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(O[C:28](=[O:30])[CH3:29])(=O)C>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:1][CH2:2][C@H:3]2[O:4][C@@H:11]([O:12][C:2](=[O:1])[CH3:3])[C@H:9]([O:10][C:5](=[O:6])[CH3:7])[C@@H:7]([O:8][C:9](=[O:10])[CH3:11])[C@@H:5]2[O:6][C:28](=[O:30])[CH3:29])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7918Acetic AnhydrideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×

Product 1

HCID 14214839HCID 14214839, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

D-Glucose (20.0 g, 0.111 mol) was placed in a 1000-mL round-bottomed flask, and pyridine (300 ml) was added. Some of glucose remained undissolved. p-Toluensulfonyl chloride (22.0 g, 0.115 mol) was added at ambient temperature. After stirring for 11 h, acetic anhydride (80 ml, 0.83 mol) was added in one portion. Gentle exothermic reaction took place. After being stirred for 1.5 h, the mixture was evaporated. Ethanol (200 ml) was added to a residual oil. The oil was dissolved and soon a white crystal appeared. After the mixture stood undisturbed at −10° C. for 27 h, the crystal was collected on a glass filter, washed with cold ethanol (25 ml, twice), and dried under reduced pressure. 6-O-(p-Toluenesulfonyl)-1,2,3,4-tetra-O-acetyl-β-D-glucose (compound 5) was obtained in 33% yield (18.5 g, 36.8 mmol).

Workup

  1. customreaction
  2. stirringAfter being stirred for 1.5 h
  3. customthe mixture was evaporated
  4. additionEthanol (200 ml) was added to a residual oil
  5. dissolutionThe oil was dissolved
  6. waitAfter the mixture stood undisturbed at −10° C. for 27 h
  7. customthe crystal was collected on a glass
  8. filtrationfilter
  9. washwashed with cold ethanol (25 ml
  10. customtwice), and dried under reduced pressure

Sources & evidence

ORD record
ord-53da285ed42646a098dfa84b063853fb
Source dataset
uspto-grants-2011_02
Patent number
US07883687B2

Reaction notes

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