Cesium carbonate → (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(3-cyclopropylprop-2-ynyloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 1175239Notes

Reaction equation

HRID 1175239 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.CC1C=CC(S(O[CH2:38][C:39]#[C:40][CH:41]2[CH2:43][CH2:42]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:38][C:39]#[C:40][CH:41]2[CH2:43][CH2:42]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 576847003-Cyclopropylprop-2-ynyl 4-methylbenzenesulfonateHCID 66704699(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol2×

Product 1

HCID 59557782(2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-(3-cyclopropylprop-2-ynyloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Procedure

Compound AW was prepared by reaction of (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D2) with 3-cyclopropylprop-2-ynyl 4-methylbenzenesulfonate (intermediate AU) in the presence of Cs2CO3 using the same procedure as described above for compound AV. 1H NMR (CD3OD): δ 7.34˜7.30 (3H, m), 7.11˜7.08 (2H, d, J=8.8 Hz), 6.86˜6.84 (2H, d, J=8.8 Hz), 4.61 (2H, d, J=1.6 Hz), 4.58 (1H, d, J=4 Hz), 4.19˜4.17 (1H, m), 4.03˜4.00 (4H, m), 3.94˜3.93 (1H, q), 3.84˜3.80 (1H, m), 3.68˜3.64 (1H, q), 1.29˜1.24 (1H, m), 0.78˜0.75 (2H, m), 0.62˜0.59 (2H, m).

Sources & evidence

ORD record
ord-f98bd98c50e64204a50de256d8f14300
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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