4'-Hydroxyacetophenone → 4-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6037Notes

Reaction equation

HRID 6037 reaction equation
Cl[C:2](Cl)(Cl)[C:3](=N)[O:4][C@H:5]1[S:22][CH2:21][C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9].OC1C=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[CH2:21][S:22][C@H:5]1[O:4][C:3]1[CH:28]=[CH:29][C:30]([C:33](=[O:35])[CH3:34])=[CH:31][CH:2]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 8000Boron trifluoride etherateHCID 216315472,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate

Product 1

HCID 150678504-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

If the procedure described in Preparation LXXXI is followed starting from 380 mg (0.882.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 100 mg (73.5.10-3 mol) of 1-(4-hydroxyphenyl)ethanone and 1.47 ml of a 0.1M solution of boron trifluoride etherate in methylene chloride, 140 mg (yield: 47%) of the expected product are obtained after crystallization from ether.

Workup

  1. customIf the procedure described in Preparation LXXXI

Sources & evidence

ORD record
ord-16997713f3d246619c9ee28f3feb0f62
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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