Trityl chloride → 5-O-Trityl-2,3-O-isopropylidene-D-ribofuranose

HRID 512126Notes

Reaction equation

HRID 512126 reaction equation
[CH3:1][C:2]1([CH3:13])[O:9][C@@H:8]2[C@@H:4]([C@@H:5]([CH2:11][OH:12])[O:6][CH:7]2[OH:10])[O:3]1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[O:9][C@@H:8]2[C@@H:4]([C@@H:5]([CH2:11][O:12][C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:6][CH:7]2[OH:10])[O:3]1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 110087122,3-O-Isopropylidene-D-ribofuranose

Product 1

HCID 105267295-O-Trityl-2,3-O-isopropylidene-D-ribofuranose

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,3-O-Isopropylidene-D-ribofuranose (15.7 g, 83.1 mmol) was dissolved in pyridine (100 mL) and trityl chloride (27.8 g, 0.1 mol) was added. The mixture was stirred at room temperature for 24 h. The solvent was evaporated and the residue purified by column chromatography on silicagel using hexanes/ethyl acetate (v.v=4:1) as eluant.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-3e295269101b4033a2d153bd0f273f52
Source dataset
uspto-grants-2015_08
Patent number
US09102634B2

Reaction notes

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