HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methyl-2-butenoic acid | HCID 10931 | — |
| Reactant | Trifluoromethanesulfonate | HCID 2758875 | — |
| Reactant | (2Z)-3-Methylhepta-2,6-dienoic acid | HCID 13947388 | — |
| Reactant | (R)-4-((2R,4S,6R)-4-Hydroxy-2-methoxy-6-phenethyl-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one | HCID 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-one | HCID 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-enoate | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666861B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-44af271fc92a46d582e51f4a003e9f3d |
| Source note | uspto-grants-2010_02 |