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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1664258Generated: October 31, 2026

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

https://huagongshe.com/reaction/1664258

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Methyl-2-butenoic acidHCID 10931—
ReactantTrifluoromethanesulfonateHCID 2758875—
Reactant(2Z)-3-Methylhepta-2,6-dienoic acidHCID 13947388—
Reactant(R)-4-((2R,4S,6R)-4-Hydroxy-2-methoxy-6-phenethyl-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 59644071—
Reactant(R)-4-((2R,4S,6R)-4-hydroxy-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 59644085—
Product(2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-phenethyl-tetrahydro-2H-pyran-4-yl 3-methylbut-2-enoateHCID 59644063—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08039465B2
Source datasetuspto-grants-2011_10
ORD IDord-6afe975191f7442481fdd181e96afb39
Source noteuspto-grants-2011_10