4-Nitrophenol → 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6034

Reaction equation

HRID 6034 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].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl.CCOCC.[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+]>[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]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 9804-NitrophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 150678484-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 25.2%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 10931941Silver imidazolateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 5.6 g (15.8.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 2 g (14.3.10-3 mol) of 4-nitrophenol, 4 g (29.3.10-3 mol) of zinc chloride and 3.8 g (21.7.10-3 mol) of silver imidazolate in 80 ml of anhydrous methylene chloride is stirred at 50° C., under an inert atmosphere, in the absence of light and in the presence of a molecular sieve (400 pm). After 48 h at this temperature, the reaction mixture is filtered on Celite®, washed with a 1N aqueous solution of hydrochloric acid, then a 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4). After evaporation to dryness, the residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 1.5 g (yield: 25%) of the expected product are obtained by precipitation in ether.

Workup

  1. filtrationthe reaction mixture is filtered on Celite®
  2. washwashed with a 1N aqueous solution of hydrochloric acid
  3. dry with materiala 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4)
  4. customAfter evaporation to dryness
  5. customthe residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

Sources & evidence

ORD record
ord-b9a267834ffc4d2eb782eaa76b1e6127
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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