1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate
![1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Structure](CAS/GIF/147126-65-6.gif)
- CAS No.
- 147126-65-6
- Chemical Name:
- 1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate
- Synonyms
- (2R,5S)-L-Methyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5S)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;(2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate;1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate;(5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate;(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl (2R,5S)-5-Acetoxy-1,3-Oxathiolane-2-Carboxylate;(2R,5S)-(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate;(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate;"2'S-isopropyl-5'R-Methyl-1'R-cyclohexyl ester (2R,5S)-5-acetoxy[1,3]oxathiolane-2-carboxylate;(2R,5S)-5-Acetyloxy-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexy
- CBNumber:
- CB61450750
- Molecular Formula:
- C16H26O5S
- Molecular Weight:
- 330.44
- MDL Number:
- MFCD28144932
- MOL File:
- 147126-65-6.mol
- MSDS File:
- SDS
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335 |
| Precautionary statements | P261-P305+P351+P338 |
| HS Code | 2934999090 |
1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate price More Price(22)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TRC | TRC-M219011-50MG | (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate | 147126-65-6 | 50mg | $294 | 2026-06-03 | Buy |
| TRC | TRC-M219011-25MG | (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate | 147126-65-6 | 25mg | $161 | 2026-06-03 | Buy |
| TRC | TRC-M219011-10MG | (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate | 147126-65-6 | 10mg | $129 | 2026-06-03 | Buy |
| Usbiological | 015931 | (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate | 147126-65-6 | 50mg | $425 | 2026-06-03 | Buy |
| aablocks | AA001EJU | (2R,5S)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate | 147126-65-6 | 25mg | $632 | 2026-05-28 | Buy |
1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Chemical Properties, Uses, Production
Chemical Properties
White Solid
Uses
Lamivudine intermediate.
Synthesis
108-24-7
147126-62-3
![1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate](/CAS/GIF/147126-65-6.gif)
147126-65-6
147027-09-6
(1R,2S,5R)-5-methyl-2-isopropylcyclohexyl-5R-hydroxy-1,3-oxathiolane-2R-carboxylate (300 g, 1.04 mol) was suspended in diisopropyl ether (1050 ml) at 0-5 °C, pyridine (103.5 g, 1.31 mol) and 4-dimethylaminopyridine (0.35 g, 3 mmol ) and stirred under nitrogen protection. Acetic anhydride (123.6 g, 1.21 mol) was diluted with diisopropyl ether (380 ml) and added dropwise to the reaction mixture at 0-8 °C over about 2 hours. The reaction was continued to be stirred at 3-8 °C for 10 h to ensure complete reaction (monitored by TLC). Upon completion of the reaction, the mixture was warmed to room temperature (20-30 °C) and diluted with diisopropyl ether. Subsequently, it was washed sequentially with 5% v/v aqueous acetic acid (2 x 400 ml) and warm water (2 x 500 ml, ca. 40 °C) to completely remove the pyridine. The organic layer was concentrated under reduced pressure at less than 45 °C to give a solid residue. Hexane (390 ml) was added to the residue, heated to about 50 °C and held for 15-20 minutes, then cooled to room temperature and stirred for 30 minutes. The product slurry was further cooled to -6°C to -10°C and stirred at that temperature for 3 hours. The product was collected by filtration and washed with pre-cooled hexane (150 ml, -6°C to -8°C). The product was dried under reduced pressure at about 45 °C for 6 h to give (2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl-5-acetoxy-1,3-oxathiolane-2-carboxylate in a yield of 279.6 g and HPLC purity (RI detector) of 99.87%. The product was a mixture of (2R,5R) and (2R,5S) isomers with (2R,5R) as the major component (≥90%) and (2R,5S) as the minor component (≤10%) as determined by HPLC (RI detector) analysis. The ratio of isomers of the acetoxy compounds had no significant effect on the ratio of α:β isomers formed in the glycosidization reaction.
References
[1] Patent: WO2010/82128, 2010, A1. Location in patent: Page/Page column 22
[2] Patent: US2011/282046, 2011, A1. Location in patent: Page/Page column 9
1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
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