21758-30-5

Basic information

• Product Name: (1R,2S,5R)-(-)-menthyl dichloroacetate
• Synonyms: (1R,2S,5R)-(-)-menthyl dichloroacetate
• CAS NO: 21758-30-5
• Molecular Weight: 267.196
• Mol File: 21758-30-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-(-)-menthyl dichloroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-(-)-menthyl dichloroacetate(21758-30-5)
• EPA Substance Registry System: (1R,2S,5R)-(-)-menthyl dichloroacetate(21758-30-5)

Safety Data

• Hazardous Substances Data: 21758-30-5(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 79-43-6 dichloro-acetic acid 
• 79-36-7 dichloroacethyl chloride 

Downstream Products

• 147027-10-9 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 
• 26315-61-7 L-menthyl glyoxylate 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 
• 764659-72-5 (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 

Relevant articles and documents

Emtricitabine synthesis method

The invention provides an emtricitabine synthesis method, which comprises: carrying out condensation on cheap and easily available dihaloacetic acid as a raw material and L-menthol, hydrolyzing to obtain menthyl glyoxylate hydrate, condensing with 2,5-dihydroxy-1,4-dithiane, carrying out halogenation, coupling with silylated 5-flucytosine, reducing, carrying out salt forming with salicylic acid toobtain emtricitabine salicylate, and finally re-crystallizing to obtain optically pure emtricitabine. According to the present invention, the whole synthesis process has characteristics of inexpensive and easily available raw materials, simple synthesis process and mild synthesis conditions, such that the synthesis cost of emtricitabine is substantially reduced; various raw materials have characteristics of good reaction selectivity and high utilization rate, such that the yield of the obtained emtricitabine is high; and the chiral substrate is easily removed during the synthesis, and the generated three-waste pollutants are less, such that the method is suitable for industrial large-scale production of emtricitabine.

Structure of Enantiomeric Menthyl (Z)-2-Chloro-3-(4-nitrophenyl)oxirane-2-carboxylates and Full Assignment of Their NMR Spectra

The major products of the Darzan condensation of (-)- and (+)-menthyl dichloroacetates with p-nitrobenzaldehyde are menthyl (Z)-2-chloro-3-(4-nitrophenyl)oxirane-2-carboxylates; the (2S,3S)-(-)- and (2R,3R)-(+)-menthyl enanthiomers were isolated.