HCID 12179943, compound → HCID 57723940, compound

HRID 1987661Notes

Reaction equation

HRID 1987661 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([OH:16])[C@@H:9]([OH:17])[CH2:8][O:7]1)=O)C>CN(C=O)C>[C:13]([O:12][C@@H:11]1[C@H:10]2[O:16][C:4](=[O:3])[C@@H:6]1[O:7][CH2:8][C@@H:9]2[OH:17])(=[O:15])[CH3:14]

Participants

3

Reactant 1

HCID 12179943HCID 12179943, compound

Product 1

HCID 57723940HCID 57723940, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R,3R,4S,5S)-3-acetoxy-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid ethyl ester (300 mg, 1.2 mmol) was dissolved in DMF (5 ml) and the solution was subjected to microwave irradiation at 150° C. for 4H. After cooling, the solvent was removed in vacuo. The crude product was purified by flash chromatography with 20% EtOAc-hexane to give (−)-(1R,4S,5S,8R)-8-acetoxy-4-hydroxy-2,6-dioxa-bicyclo[3.2.1]octan-7-one.

Workup

  1. customirradiation at 150° C. for 4H
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-18003f89f138442283ea18fe224f7bd1
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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