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

Temperature

50 °C

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.

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

ORD record

ord-b9a267834ffc4d2eb782eaa76b1e6127

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246961