Trityl chloride → HCID 53667752, compound

HRID 1457536Notes

Reaction equation

HRID 1457536 reaction equation
[C@@H:1]1([N:12]=[N+:13]=[N-:14])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].Cl[C:16]([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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[C:39](=[O:41])[CH3:40])(=O)C>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:2]([O:3][C@@H:2]1[C@@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@H:6]([O:7][C:39](=[O:41])[CH3:40])[C@@H:8]([CH2:10][O:11][C:16]([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)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][C@H:1]1[N:12]=[N+:13]=[N-:14])(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 7918Acetic AnhydrideHCID 11074507HCID 11074507, compound

Product 1

HCID 53667752HCID 53667752, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Composition 4 (3.05 g) was dissolved in dry pyridine (50 ml), chlorotriphenyl-methane (5.01 g) was added and the reaction mixture was stirred at 70° C. for three hours. It was cooled to 0° C., acetic anhydride (6.36 ml) was added dropwise and the mixture was stirred overnight at room temperature. It was poured into ice-water and was diluted with chloroform (300 ml). The organic layer was washed subsequently with water, 2M hydrochloric acid, water, was dried and evaporated to leave 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranosyl azide (5, 7.67 g, 90%).

Workup

  1. temperatureIt was cooled to 0° C.
  2. stirringthe mixture was stirred overnight at room temperature
  3. washThe organic layer was washed subsequently with water, 2M hydrochloric acid, water
  4. customwas dried
  5. customevaporated

Sources & evidence

ORD record
ord-668aa8778ec945bfb39b703fbe88494e
Source dataset
uspto-grants-1998_12
Patent number
US05849709

Reaction notes

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