Trifluoromethanesulfonate → (Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

HRID 1664256Notes

Reaction equation

HRID 1664256 reaction equation
[O-]S([C:5](F)(F)F)(=O)=O.[OH:9][C@H:10]1[CH2:15][C@@H:14]([CH2:16][CH2:17][C@H:18]([CH3:21])[CH:19]=[CH2:20])[O:13][C@:12]([C@@H:24]2[CH2:28][S:27][C:26](=[O:29])[N:25]2[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)([O:22][CH3:23])[CH2:11]1.O[C@H:40]1[CH2:45][C@@H:44](CCCC=C)[O:43][C@:42]([C@@H:53]2[CH2:57]SC(=O)N2CC2C=CC(OC)=CC=2)(OC)[CH2:41]1>>[CH3:5]/[C:40](/[CH2:41][CH2:42][CH:53]=[CH2:57])=[CH:45]/[C:44]([O:9][C@@H:10]1[CH2:15][C@@H:14]([CH2:16][CH2:17][C@H:18]([CH3:21])[CH:19]=[CH2:20])[O:13][C@@:12]([O:22][CH3:23])([C@@H:24]2[CH2:28][S:27][C:26](=[O:29])[N:25]2[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[CH2:11]1)=[O:43]

Participants

4

Reactant 3

HCID 2758875Trifluoromethanesulfonate2×HCID 59644066(R)-4-((2R,4S,6R)-4-Hydroxy-2-methoxy-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 59644085(R)-4-((2R,4S,6R)-4-hydroxy-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

Product 1

HCID 25215543(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-4-yl) 3-Methylhepta-2,6-dienoate

Procedure

Triflate formation using the method shown in Example 22, with the modification that (R)-4-((2R,4S,6R)-4-hydroxy-2-methoxy-6-((S)-3-methylpent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one was substituted for (R)-4-((2R,4S,6R)-4-hydroxy-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one, followed by triflate displacement using the method shown in Example 23, afforded the title compound.

Sources & evidence

ORD record
ord-c3e17a460b83440abe83591c6fd28ef8
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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