Reaction #1447108

ord-2f17205d54424b77ae3d4485f77e18ff

Reaction equation

CCOC(=O)N=NC(=O)OCC
Diethyl azodicarboxylate
CCc1ccc(Cc2cc(C3(O)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)cc(O)c2C)cc1
3-(4-ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene
OC1CCC1
cyclobutanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
→
CCc1ccc(Cc2cc(C3(O)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)cc(OC3CCC3)c2C)cc1
1-Cyclobutoxy-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

Reactants

CCOC(=O)N=NC(=O)OCC
Diethyl azodicarboxylate
CCc1ccc(Cc2cc(C3(O)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)cc(O)c2C)cc1
3-(4-ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene
OC1CCC1
cyclobutanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine

Reagents

None

Solvents

C1CCOC1
THF
C1CCOC1
THF

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture is heated
  2. 2
    TemperatureAfter cooling to room temperature
  3. 3
    Otherthe solvent is evaporated
  4. 4
    Otherthe residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel

Procedure

Diethyl azodicarboxylate (0.38 g) dissolved in THF (0.5 mL) is added to 3-(4-ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.27 g), cyclobutanol (0.1 mL) and triphenylphosphine (0.56 g) dissolved in THF (2 mL). The mixture is heated with stirring at 70° C. overnight. After cooling to room temperature, the solvent is evaporated and the residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07879807B2uspto-grants-2011_02