Reaction #2146751

ord-1c1c51f280a14699bc26e6b978be0d32

Reaction equation

O=C(OC[C@H]1O[C@H](OC(=O)c2ccccc2)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1
(2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one
C#[C][Mg][Br]
ethynylmagnesium bromide
→
C#C[C@]1(O)[C@@H](OC(=O)c2ccccc2)O[C@H](COC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1
(2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-3-ol

Reactants

O=C(OC[C@H]1O[C@H](OC(=O)c2ccccc2)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1
(2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one
C#[C][Mg][Br]
ethynylmagnesium bromide

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheris −30° C.

Procedure

Alternatively, the same procedure as that described in step 2 can be used, except that the reaction temperature is −30° C. and the reaction time is 3 hours, using (2R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-dihydrofuran-3-one (1.0 g, 2.17 mmol, 1.0 equiv.), 1M ethynylmagnesium bromide (13 ml, 6.51 mmol, 3 equiv.) CeCl3 (1.77 g, 7.16 mmol, 3.3 equiv.) and THF (18 ml), to give (2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-3-ol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08278282B2uspto-grants-2012_10