L-Menthyl 2,2-Dihydroxyacetate

CAS: 111969-64-3

Ref. TR-M219145

Product Information

• Name: L-Menthyl 2,2-Dihydroxyacetate
• Synonyms: 2,2-Dihydroxyacetic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester, Dihydroxyacetic Acid (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl Ester, [1R-(1alpha,2beta,5alpha)]-Dihydroxyacetic Acid 5-Methyl-2-(1-methylethyl)cyclohexyl Ester, 2,2-Dihydroxyacetic Acid (-)-Menthyl Ester, (1R,2S,5R)-5-Methyl-2-(1-Methylethyl)Cyclohexyl Dihydroxy-Acetate, (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl 2,2-dihydroxyacetate, (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexyl dihydroxyacetate, Acetic acid, 2,2-dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, Acetic acid, dihydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, Acetic acid, dihydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, [1R-(1α,2β,5α)]-, Glyoxylic acid (1S)-menthyl ester hydrate, L-Menthyl glyoxylate hydrate, L-Mgh
• CAS: 111969-64-3

Description

Applications L-Menthyl 2,2-Dihydroxyacetate is used as a reagent in the synthesis of Lamivudine (L172500); a potent nucleoside reverse transcriptase inhibitor used for the treatment of chronic hepatitis B. L-Menthyl 2,2-Dihydroxyacetate is also used as a reagent in the synthesis of 4-acetoxy-3-hydroxyethylazetidin-2-one, a key intermediate for the preparation of penem and carbapenem antibiotics.
References Morris, D.M., J. Pharm. Biomed. Anal., 12, 255 (1944); Nevens, B.F., et al.: Gastroenterology, 113, 1258 (1997); Perry, C.M., et al.: Drugs, 53, 657 (1977); Goodyear, M.D., et al.: Tetrahedron Lett., 46, 8535 (2005); Kametani, T., et al.: Heterocycles, 25, 241 (1987)

• Brand: TRC

Chemical properties

• Molecular weight: 230.3
• Formula: C₁₂H₂₂O₄
• Color/Form: White to Off-White Solid
• InChI: InChI=1S/C12H22O4/c1-7(2)9-5-4-8(3)6-10(9)16-12(15)11(13)14/h7-11,13-14H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
• InChI key: InChIKey=BWZMJRSMHQDFIT-KXUCPTDWSA-N
• SMILES: CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(O)O