(2R,4R,5R)-5-((Benzoyloxy)methyl)-3-oxotetrahydrofuran-2,4-diyl dibenzoate → (2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-3-ol

HRID 2059569Notes

Reaction equation

HRID 2059569 reaction equation
[C:1]([O:9][C@@H:10]1[C:14](=[O:15])[C@H:13]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:12]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([Mg]Br)#[CH:36]>C1COCC1>[C:1]([O:9][C@@H:10]1[C@:14]([C:35]#[CH:36])([OH:15])[C@H:13]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:12]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10072943(2R,4R,5R)-5-((Benzoyloxy)methyl)-3-oxotetrahydrofuran-2,4-diyl dibenzoateHCID 178418486HCID 178418486, compound

Product 1

HCID 86642243(2R,3R,4R,5R)-2,4-dibenzoyloxy-5-benzoyloxymethyl-3-ethynyl-tetrahydrofuran-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customis −30° C.

Sources & evidence

ORD record
ord-1c1c51f280a14699bc26e6b978be0d32
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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