Dichloromethane → D-Ribofuranosyl chloride, tribenzoate

HRID 843506Notes

Reaction equation

HRID 843506 reaction equation
C(O[C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[Cl:38]CCl>[Ti](Cl)(Cl)(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:27][CH:5]1[Cl:38])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6344Dichloromethane2×HCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 12806354D-Ribofuranosyl chloride, tribenzoate

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

To a solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (3.02 g, 5.98 mmol) in dry dichloromethane (100 ml) was added via cannula a dichloromethane solution of titanium tetrachloride (1.13 g, 5.98 mmol, 5.98 ml of a 1M solution). The solution was stirred at room temperature for 1. 5 hours under argon, then washed with water (3×100 ml), dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compounds as a colourless oil (2.9 g, 1 00%). 1H nmr indicated it to be an approximately 1:1 mixture of α:β-anomers.

Workup

  1. wash5 hours under argon, then washed with water (3×100 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-8aeccc2ad7d64c60bdbb7626ef31db69
Source dataset
uspto-grants-2002_04
Patent number
US06379911B2

Reaction notes

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