Réaction #321789

ord-e54263faa9a44790b76fd9dc4b236ec2

Équation de réaction

C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)C(O)S(=O)(=O)c1ccc(C)cc1
compound
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)C(O)S(=O)(=O)c1ccc(C)cc1
1-para-Toluenesulfonyl-3-isopropenyl-4,5-di-O-methyl-β-D-psicopyranos
[I-].[Na+]
sodium iodide
→
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CI
desired product
Rendement 88.0%
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CI
1-Desoxy-1-iodo-3-isopropenyl-4,5-di-O-methyl-β-D-psicopyranose
Rendement 88.0%

Réactifs

C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)C(O)S(=O)(=O)c1ccc(C)cc1
compound
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)C(O)S(=O)(=O)c1ccc(C)cc1
1-para-Toluenesulfonyl-3-isopropenyl-4,5-di-O-methyl-β-D-psicopyranos
[I-].[Na+]
sodium iodide

Réactifs

Aucun

Solvants

CC(C)=O
acetone
CCCCC.CCOCC
diethyl ether pentane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autredescribed for the preparation of Example 12

Mode opératoire

Following the procedure described for the preparation of Example 12, starting from 0.10 g (0.25 mmol) of the compound obtained in Example 30 and 0.18 g (1.20 mmol) of sodium iodide in 3 ml of acetone at room temperature, then purification by chromatography on silica gel (eluant: diethyl ether/pentane, 1.5:1), 0.079 g (0.22 mmol) of the desired product in the form of a pale-yellow-coloured solid is obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05595976uspto-grants-1997_01