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

HRID 1664257Notes

Reaction equation

HRID 1664257 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:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][C@:12]([C@@H:26]2[CH2:30][S:29][C:28](=[O:31])[N:27]2[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)([O:24][CH3:25])[CH2:11]1.O[C@H:42]1[CH2:47][C@@H:46](CCCC=C)[O:45][C@:44]([C@@H:55]2[CH2:59]SC(=O)N2CC2C=CC(OC)=CC=2)(OC)[CH2:43]1>>[CH3:5]/[C:42](/[CH2:43][CH2:44][CH:55]=[CH2:59])=[CH:47]/[C:46]([O:9][C@@H:10]1[CH2:15][C@@H:14]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:13][C@@:12]([O:24][CH3:25])([C@@H:26]2[CH2:30][S:29][C:28](=[O:31])[N:27]2[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[CH2:11]1)=[O:45]

Participants

4

Reactant 3

HCID 2758875Trifluoromethanesulfonate2×HCID 59644071(R)-4-((2R,4S,6R)-4-Hydroxy-2-methoxy-6-phenethyl-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 59644081(Z)-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-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-phenethyl-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one is 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, affords the title compound.

Sources & evidence

ORD record
ord-2b330662a39b45ceab0d94350e8bf645
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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