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

HRID 512127
Notes
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Reaction equation

HRID 512127 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(N(CC)CC)C.[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>ClCCl.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:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:6][CH:7]2[OH:10])[O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 110087122,3-O-Isopropylidene-D-ribofuranose

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2,3-O-Isopropylidene-D-ribofuranose (20 g, 105.2 mmol) was dissolved in dichloromethane (200 mL) at 0° C. Triethylamine (10.9 g, 107.5 mmol) and a catalytic. amount of pyridine were added to the reaction mixture, followed by the addition of trityl chloride (27.8 g, 0.1 mol). The mixture was stirred at 0° C. for 3 h and further 12 h at room temperature. To the reaction mixture was added saturated aqueous sodium bicarbonate (80 mL) and the phases were separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvents were removed in vacuo. The crude product was used without further purification in the next step.

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvents were removed in vacuo
  5. customThe crude product was used without further purification in the next step

Sources & evidence

ORD record
ord-55fd257797124acc83119f9d3a03811e
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102634B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes