Toluene → 1,6-anhydro-3,4-dideoxy-2-O-phenylcarbamoyl-beta-D-threo-hex-3-enopyranose

HRID 1769246Notes

Reaction equation

HRID 1769246 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[C@@H:17]12[O:25][CH2:24][C@@H:22]([O:23]1)[CH:21]=[CH:20][C@@H:18]2[OH:19]>C(N(CC)CC)C>[C:1]1([NH:7][C:8]([O:19][C@H:18]2[CH:20]=[CH:21][C@H:22]3[CH2:24][O:25][C@@H:17]2[O:23]3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7672Phenyl isocyanateHCID 118047741,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose

Product 1

HCID 867483871,6-anhydro-3,4-dideoxy-2-O-phenylcarbamoyl-beta-D-threo-hex-3-enopyranoseYield 86.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.56 g of phenyl isocyanate was added at room temperature to 30 ml of a dry toluene solution containing 0.3 g of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose under an inert atmosphere of nitrogen gas. Further, 0.1 ml of triethylamine was added thereto, and the reaction mixture was refluxed under heating for two hours. Completion of the reaction was confirmed by thin layer chromatography, and then the solvent was immediately distilled off under reduced pressure to obtain a syrup crude product. This crude product was purified by silica gel chromatography (ethyl acetate: hexane=1:3) to obtain 0.5 g of the desired product (Compound No. 23). The NMR analytical data of this product are as follows.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureunder heating for two hours
  3. distillationthe solvent was immediately distilled off under reduced pressure
  4. customto obtain a syrup crude product
  5. customThis crude product was purified by silica gel chromatography (ethyl acetate: hexane=1:3)

Sources & evidence

ORD record
ord-08c9d44c2ffa44f0bea92146583bbce3
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

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