1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate

Product Name: 1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate
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;"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;(2R,5S)-5-(Acetyloxy)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl -2-(1-methylethyl)cyclohexyl Ester
CBNumber: CB61450750
Molecular Formula: C16H26O5S
Formula Weight: 330.44
MOL File: 147126-65-6.mol

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1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Property

Boiling point:: 412.5±45.0 °C(Predicted)
Density: 1.16±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Methanol
form: Solid
color: White

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Safety

HS Code: 2934999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: M219011
Product name: (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
Packaging: 100mg
Price: $405
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: APN0002093
Product name: (2R,5S)-L-MENTHOL-5-(ACETYLOXY)-1,3-OXATHIOLANE-2-CARBOXYLATE
Purity: 95.00%
Packaging: 5MG
Price: $496.73
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 65901
Product name: (2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate
Packaging: 10mg
Price: $625
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0004564
Product name: (2R,5S)-L-MENTHYL-5-(ACETYLOXY)-1,3-OXATHIOLANE-2-CARBOXYLATE
Purity: 95.00%
Packaging: 50MG
Price: $697.34
Updated: 2021/12/16

SynQuest Laboratories

Product number: 6H70-1-01
Product name: (5R)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
Packaging: 250mg
Price: $1000
Updated: 2021/12/16

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1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

Lamivudine intermediate.

Synthesis

108-24-7

147126-62-3

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

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147126-65-6, 1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylateRelated Search:

ISO-AMYL THIOGLYCOLATE menglytate 1,3-OXATHIOLANE-2-CARBOXYLIC ACID, 5-HYDROXY- 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

(2R,5S)-5-(Acetyloxy)-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl -2-(1-methylethyl)cyclohexyl Ester

(2R,5S)-L-Menthyl-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

(2R,5S)-L-Methyl-5-(acetyloxy)-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)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate

(2R,5S)-(1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-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-methylethyl)cyclohexyl ester,(2R,5S)- (9CI)

1,3-Oxathiolane-2-carboxylic acid, 5-(acetyloxy)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, (2R,5S)- (9CI)

(2R,5S)-5-Acetyloxy-1,3-oxathiolane-2-carboxylic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexy

147126-65-6

C16H26O5S

Heterocycles

Sulfur & Selenium Compounds

Chiral Reagents