Reaction #159767

Reaction equation

compound

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-tetrahydro-pyran-2-ol

HCl

→

2-Methoxy-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-benzaldehyde

Yield 71.0%

Solvents

THF

Conditions

Workup

1. 1
   ConcentrationThis reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with ethyl acetate (100 mL)
3. 3
   Washwashed with sat. NH4Cl (20 mL)
4. 4
   Dryingdried over sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified by silica gel column chromatography

Procedure

To a stirred solution of compound prepared in step II (4.80 g, 6.68 mmol) in THF (20 mL) was added 6N HCl (10 mL) and stirred for 16 h. This reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate (100 mL) washed with sat. NH4Cl (20 mL), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 2-Methoxy-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-benzaldehyde (3.2 g).

Source