반응 #1463160

반응 방정식

(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)phenyl]-D-glucitol

→

3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzaldehyde

수율 100.3%

용매

chloroform

반응 조건

후처리

1. 1
   온도the mixture was refluxed
2. 2
   기타After separating the insoluble matter from the reaction mixture
3. 3
   여과by filtration through celite at room temperature
4. 4
   농축the filtrate was concentrated
5. 5
   기타The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

실험 절차

Manganese dioxide (20.4 g) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)phenyl]-D-glucitol (6.8 g) obtained in Reference Example 24 in chloroform (100 ml) and the mixture was refluxed with stirring for 1.5 hours. After separating the insoluble matter from the reaction mixture by filtration through celite at room temperature, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzaldehyde (6.8 g).

출처