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

HRID 1290446Notes

Reaction equation

HRID 1290446 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.[F-].P([O-])(O)(O)=O.[K+]>O1CCCC1.C(OCC)(=O)C>[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

7

Reactant 4

HCID 176Acetic Acid2×HCID 28179Fluoride IonHCID 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 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.54 g of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4thioribofuranose (prepared by the procedure of J. A. Secrist et al., J. Med. Chem.,1992, 35, 533) in 8 ml of tetrahydrofuran and 0.6 g of acetic acid is added 4 mmol of 1M n-tetrabutylamnonium fluoride solution. The reaction is stirred for 5 hours and then another portion of 0.10 g of acetic acid and 1 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. stirringthe reaction is stirred for 1 hour
  3. customPurification by chromatography

Sources & evidence

ORD record
ord-fe72e6f04abd429498c639d44cbd4a1b
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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