Réaction #321788

ord-3ea937f0093f4073bbd3b1a6655a5040

Équation de réaction

C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CO
compound
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CO
3-Isopropenyl-4,5-di-O-methyl-β-D-psicopyranose
Cc1ccc(S(=O)(=O)Cl)cc1
tosyl chloride
→
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)C(O)S(=O)(=O)c1ccc(C)cc1
desired product
Rendement 70.8%
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
Rendement 70.8%

Réactifs

C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CO
compound
C=C(C)[C@@]1(O)[C@H](OC)[C@H](OC)CO[C@]1(O)CO
3-Isopropenyl-4,5-di-O-methyl-β-D-psicopyranose
Cc1ccc(S(=O)(=O)Cl)cc1
tosyl chloride

Réactifs

Aucun

Solvants

CCCCC.CCOCC
diethyl ether pentane
c1ccncc1
pyridine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autredescribed for the preparation of Example 10

Mode opératoire

Following the procedure described for the preparation of Example 10, starting from 0.80 g (3.22 mmol) of the compound obtained in Example 29 and 1.53 g of tosyl chloride in 15 ml of anhydrous pyridine, then purification by chromatography on silica gel (eluant: diethyl ether/pentane, 2:1), 0.92 g (2.28 mmol) of the desired product in the form of a white-coloured foam is obtained.

Source

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