3-Methyl-2-butenoic acid → (2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl 3-methylbut-2-enoate

HRID 2251770Notes

Reaction equation

HRID 2251770 reaction equation
[O-]S(C(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]1C[C@@H](CCCC=C)O[C@]([C@@H]2CSC(=O)N2CC2C=CC(OC)=CC=2)(OC)C1.[CH3:70][C:71]([CH3:76])=[CH:72][C:73](O)=[O:74].C/C(/CCC=C)=C/C(O)=O>>[CH3:70][C:71]([CH3:76])=[CH:72][C:73]([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:74]

Participants

6

Reactant 5

HCID 109313-Methyl-2-butenoic acidHCID 2758875Trifluoromethanesulfonate2×HCID 13947388(2Z)-3-Methylhepta-2,6-dienoic acidHCID 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 59644063(2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl 3-methylbut-2-enoate

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, with the modification that 3-methyl-2-butenoic acid is substituted for (Z)-3-methylhepta-2,6-dienoic acid, affords the title compound.

Sources & evidence

ORD record
ord-9e8e79c727604e52a07ad5a1c25914bf
Source dataset
uspto-grants-2008_01
Patent number
US07320974B2

Reaction notes

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