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

Base Information

• Chemical Name: 1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate
• CAS No.: 147126-65-6
• Molecular Formula: C16H26 O5 S
• Molecular Weight: 330.445
• Hs Code.: 2934999090
• Mol file: 147126-65-6.mol

Synonyms:1,3-Oxathiolane-2-carboxylicacid, 5-(acetyloxy)-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, [1R-[1a(2R*,5S*),2b,5a]]-

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

Chemical Property:

• Refractive Index: 1.511
• Boiling Point: 412.5±45.0 °C(Predicted)
• PSA: 87.13000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 2.96910
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R,5S)-L-Menthol-5-(acetyloxy)-1,3-oxathiolane-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 3 articles about 1,2,5-Menthyl-5(S)-acetoxy-[1,3]-oxathiolene-2-(R)-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

acetic anhydride (108-24-7) + (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147126-65-6,147126-67-8) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8)

Guidance literature:

With pyridine; dmap; In di-isopropyl ether; at 0 - 8 ℃; for 12h; Inert atmosphere;

Reference yield:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate (200396-19-6) + acetic anhydride (108-24-7) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147126-65-6,147126-67-8) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2S,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147126-67-8) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147027-09-6,147126-67-8) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2S,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147126-67-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; Overall yield = 91 %; Overall yield = 2.34 g; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00982

Reference yield:

L-menthyl glyoxylate monohydrate (111969-64-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate (147126-65-6,147126-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / toluene / 2 h / 120 °C / Dean-Stark

1.2: 4 h / Reflux

1.3: 16 h / 0 °C

2.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; acetic acid; In dichloromethane; toluene;

DOI:10.1021/acs.orglett.5b00982

upstream raw materials:

acetic anhydride

(2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester

L-menthyl glyoxylate monohydrate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate

Downstream raw materials:

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF CIS-NUCLEOSIDE DERIVATIVE". Page/Page column 9. . Retrieved 2011/11/30.