4-Toluenesulfonyl chloride → [(2R,3S)-3-hydroxytetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate

HRID 1928580Notes

Reaction equation

HRID 1928580 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([OH:8])[CH2:6][CH2:5][O:4]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:1][CH2:2][C@@H:3]2[C@@H:7]([OH:8])[CH2:6][CH2:5][O:4]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1246571,2-Dideoxyribofuranose

Product 1

HCID 58271236[(2R,3S)-3-hydroxytetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonateYield 97.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol (1.59 g, 13.46 mmol) (prepared as described in Chenault, K. H.; Mandes, R. F. Tetrahedron, 1997, 53(32), 11033-11038) is dissolved in dry pyridine (15 mL) and the solution cooled to −40° C. in a dry ice/acetone bath for 30 min. p-Toluenesulfonyl chloride (2.58 g, 13.51 mmol) is added slowly over 5 min and the solution allowed to warm up to room temperature over 4 h. The solution is concentrated to provide 3.59 g (86%) of the title compound which is used without further purification. LC-ES/MS m/z 295.0 [M+Na]+, TR=1.76 min. (Symyx Draw 3.1 (IUPAC Name) provides the name for the compound of Preparation 12.)

Workup

  1. additionis added slowly over 5 min
  2. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-bf0d0318235c4d3b94817b3c9c1c786d
Source dataset
uspto-grants-2012_05
Patent number
US08183388B2

Reaction notes

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