2,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide → 6-acetyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 1685416Notes

Reaction equation

HRID 1685416 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@@H:6]1Br)(=[O:3])[CH3:2].[C:20]([C:23]1[N:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)(=[O:22])[CH3:21]>[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+].C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:29][C:26]1[CH:27]=[N:28][C:23]([C:20](=[O:22])[CH3:21])=[CH:24][CH:25]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromideHCID 124162311-(5-Hydroxypyridin-2-yl)ethan-1-one

Product 1

HCID 672924216-acetyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 15%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 10931941Silver imidazolateCatalystHCID 6342AcetonitrileSolvent

Procedure

1.29 g (9.47 mM) of zinc chloride are melted and left to cool to room temperature. 4 g of 13× molecular sieve, 50 ml of acetonitrile, 3.1 g (8.7 mM) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1.4 g (8 mM) of silver imidazolate and 1 g (7.3 mM) of 6-acetyl-3-pyridinol are added. The mixture is stirred for 3 hours at 65° C. After filtration, the material on the filter is rinsed with ethyl acetate and the volatile solvents are evaporated off under reduced pressure. The product is purified by chromatography on silica gel using a toluene/isopropanol mixture (98/2; v/v) as the eluent. The purified product is crystallized from isopropyl alcohol to give the expected product in the form of a white solid with a yield of 15%.

Workup

  1. waitleft
  2. filtrationAfter filtration
  3. washthe material on the filter is rinsed with ethyl acetate
  4. customthe volatile solvents are evaporated off under reduced pressure
  5. customThe product is purified by chromatography on silica gel using a toluene/isopropanol mixture (98/2; v/v) as the eluent
  6. customThe purified product is crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-b050b5aa995a4e4b8f3c64d1b2bdd97d
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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