Acetic Acid → (2R)-5-(Acetyloxy)tetrahydro-2-thiophenemethanol

HRID 54830Notes

Reaction equation

HRID 54830 reaction equation
[C:1]([O:4][CH:5]1[S:9][C@H:8]([CH2:10][O:11][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(O)(=O)C.P([O-])(O)(O)=O.[K+].C(OCC)(=O)C>O1CCCC1>[C:1]([O:4][CH:5]1[S:9][C@@H:8]([CH2:10][OH:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 8857Ethyl AcetateHCID 516951Monobasic potassium phosphateHCID 151260981-O-Acetyl-5-O-t-butyldiphenylsilyl-4-thio-2,3-dideoxyribofuranose

Product 1

HCID 54182721(2R)-5-(Acetyloxy)tetrahydro-2-thiophenemethanolYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.54 g of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose (prepared by the procedure of J. A. Secrist et al., J. Meal. Chem.,1992, 35, 533) in 8 ml of tetrahydrofuran and 0.6 g of acetic acid is added 4 mmol of 1M n-tetrabutylammonium fluoride solution. The reaction is stirred for 5 hours and then another portion of 0.10 g of acetic acid and I mmol of n-tetrabutylammonium fluoride is added and the reaction is stirred for 1 hour. Cold potassium dihydrogen phosphate and ethyl acetate are added to the reaction mixture, followed by an aqueous workup. Purification by chromatography gives 0.164 g of the desired product.

Workup

  1. customprepared by the procedure of J
  2. additionis added
  3. stirringthe reaction is stirred for 1 hour
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-a99e727574c344ae8230b4534d34b25e
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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