p-Toluenesulfonic acid → HCID 86747466, compound

HRID 1197628Notes

Reaction equation

HRID 1197628 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C.[C:19]([O:27][CH2:28][C@H:29]1[O:37][C@@:32]([O:35][CH3:36])([CH2:33][OH:34])[C@@H:31]([OH:38])[CH2:30]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OC[C@H]1O[C@](OC)(CO)[C@@H](O)C1)(=O)C1C=CC=CC=1>CO>[C:19]([O:27][CH2:28][C@H:29]1[O:37][C:32]([O:35][CH3:36])([CH2:33][OH:34])[C@@H:31]([OH:38])[CH2:30]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 67680903HCID 67680903, compound3×HCID 86747467HCID 86747467, compound4×

Product 1

HCID 86747466HCID 86747466, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Step 5 (5.6 g) in anhydrous methanol (140 mL) containing p-toluenesulfonic acid (374 mg) was refluxed for 30 min. The reaction mixture was cooled and neutralized with triethylamine. The solution was evaporated to dryness and applied on a column of silica gel equilibrated and eluted with etylacetate-ethanolhexane (10:1:10). Two fractions were obtained, methyl 6-O-benzoyl-4-deoxy-α-D-fructofuranoside and methyl 6-O-benzoyl-4-deoxy-β-D-fructofuranoside; methyl 6 -O-benzoyl-4-deoxy-β-D-fructofuranoside was the more polar of the two. The yield of methyl 6-O-benzoyl-4-deoxy-α-D-fructofuranoside was 2.45 g (syrup). The yield of methyl 6-O-benzoyl-4-deoxy-β-D-fructofuranoside was 1.47 g. The structures of methyl 6-O-benzoyl-4-deoxy-α-D-fructofuranoside and methyl 6-O-benzoyl-4-deoxy-β-D-fructofuranoside were established by 1H and 13C nmr.

Workup

  1. temperaturewas refluxed for 30 min
  2. temperatureThe reaction mixture was cooled
  3. customThe solution was evaporated to dryness
  4. washeluted with etylacetate-ethanolhexane (10:1:10)
  5. customTwo fractions were obtained

Sources & evidence

ORD record
ord-a2f4f0f273b44e488ee11785a2650a18
Source dataset
uspto-grants-1994_01
Patent number
US05276143

Reaction notes

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