Trityl chloride → p-Nitrophenyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-glucopyranoside

HRID 1899760Notes

Reaction equation

HRID 1899760 reaction equation
[O:1]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[C:46](=[O:48])[CH3:47])(=O)C>N1C=CC=CC=1>[C:2]([O:4][C@@H:3]1[C@@H:5]([O:6][C:5](=[O:6])[CH3:7])[C@H:7]([O:8][C:46](=[O:48])[CH3:47])[C@@H:9]([CH2:11][O:12][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:10][C@H:2]1[O:1][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 6456Trityl chloride2×HCID 7918Acetic AnhydrideHCID 92930p-Nitrophenyl beta-D-glucopyranoside

Product 1

HCID 14682815p-Nitrophenyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-glucopyranosideYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

In a 100-ml round-bottomed flask, 1.42 g of p-nitrophenyl β-D-glucopyranoside and 1.5 g of anhydrous trityl chloride are introduced into 10 ml of anhydrous pyridine, and the flask is left in the dark with stirring at 40° C. The reaction is followed by TLC, adding trityl chloride if necessary. After 24 hours, the flask is brought to room temperature and 6 ml of acetic anhydride are added. The reaction medium is left for 48 hours with stirring, the reaction being followed by TLC (silica gel, ether/petroleum ether, 7:3); it is taken up in 500 ml of ice-cold water and stirred for 2 hours. The mixture is then filtered through celite and the celite is rinsed with dichloromethane. The organic phase is washed successively with ice-cold water, 10% strength hydrochloric acid, saturated aqueous sodium bicarbonate solution and then ice-cold water. It is dried over sodium sulphate and concentrated under vacuum at 35° C. The residue is chromatographed on a column of silica, eluting with a 7:3 ether/petroleum ether mixture. The fractions containing the heteroside are combined and concentrated under vacuum at 35° C. 2.6 g of an oil are obtained (yield=83%), the product being pure in TLC: silica gel, ether/petroleum ether (7:3), Rf=0.33.

Workup

  1. waitthe flask is left in the dark
  2. customis brought to room temperature
  3. waitThe reaction medium is left for 48 hours
  4. stirringwith stirring
  5. stirringstirred for 2 hours
  6. filtrationThe mixture is then filtered through celite
  7. washthe celite is rinsed with dichloromethane
  8. washThe organic phase is washed successively with ice-cold water, 10% strength hydrochloric acid, saturated aqueous sodium bicarbonate solution
  9. dry with materialIt is dried over sodium sulphate
  10. concentrationconcentrated under vacuum at 35° C
  11. customThe residue is chromatographed on a column of silica
  12. washeluting with a 7:3 ether/petroleum ether mixture
  13. additionThe fractions containing the heteroside
  14. concentrationconcentrated under vacuum at 35° C

Sources & evidence

ORD record
ord-7948962041cf492caf3181030d8336af
Source dataset
uspto-grants-1996_11
Patent number
US05573926

Reaction notes

Loading…