(R)-4-((2R,4R,6R)-6-ethyl-2,4-dihydroxy-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one → (R)-4-((2R,4R,6R)-6-Ethyl-4-hydroxy-2-methoxy-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

HRID 1664251Notes

Reaction equation

HRID 1664251 reaction equation
[CH2:1]([C@H:3]1[O:8][C@:7]([C@@H:10]2[CH2:14][S:13][C:12](=[O:15])[N:11]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)([OH:9])[CH2:6][C@H:5]([OH:25])[CH2:4]1)[CH3:2].O[C@:27]1([C@@H]2CSC(=O)N2CC2C=CC(OC)=CC=2)C[C@@H](O)C[C@@H](CCCC=C)O1>>[CH2:1]([C@H:3]1[O:8][C@:7]([C@@H:10]2[CH2:14][S:13][C:12](=[O:15])[N:11]2[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)([O:9][CH3:27])[CH2:6][C@H:5]([OH:25])[CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 59644048(R)-4-((2R,4R,6R)-6-ethyl-2,4-dihydroxy-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 59644061(R)-4-((2R,4S,6R)-2,4-dihydroxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

Product 1

HCID 59644044(R)-4-((2R,4R,6R)-6-Ethyl-4-hydroxy-2-methoxy-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

Procedure

Application of the method shown in Example 13, with the modification that (R)-4-((2R,4R,6R)-6-ethyl-2,4-dihydroxy-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one was substituted for (R)-4-((2R,4S,6R)-2,4-dihydroxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one, afforded the title compound.

Sources & evidence

ORD record
ord-c177664103f742b5a818f9d97324d80a
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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