26315-61-7

Basic information

• Product Name: (1R)-(-)-Menthyl glyoxylate hydrate
• Synonyms: Glyoxylic acid (1R)-menthyl ester hydrate;L-MENTHYL GLYOXYLATE;(L)-METHYLGLYOXYLATE HYDRATE;(1R)-(-)-MENTHYL GLYOXYLATE HYDRATE;(1R)-Menthylesterhydrate;(1R,2S,5R)-2-isopropyl-5-Methylcyclohexyl 2-oxoacetate hydrate
• CAS NO: 26315-61-7
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 230.3
• EINECS: -0
• Product Categories: chiral
• Mol File: 26315-61-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 76-78°C
• Boiling Point: 95-96°C 0,3mm
• Flash Point: 95-96°C/0.3mm
• Appearance: /
• Density: 1,182 g/cm3
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.458
• Sensitive: Air Sensitive
• BRN: 5637371
• CAS DataBase Reference: (1R)-(-)-Menthyl glyoxylate hydrate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-Menthyl glyoxylate hydrate(26315-61-7)
• EPA Substance Registry System: (1R)-(-)-Menthyl glyoxylate hydrate(26315-61-7)

Safety Data

• Statements: 51/53
• Safety Statements: 61
• RIDADR: 3077
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 26315-61-7(Hazardous Substances Data)

Usage

General Description

"(1R)-(-)-Menthyl glyoxylate hydrate is a chemical compound commonly used as an asymmetric synthesis reagent in chemical reactions. Its molecular formula is C14H26O5 and it is characterized by a crystalline solid form and a characteristic minty odor, derived from its relation to menthol. It has a specific rotation of -50 ° (c=1, MeOH) and a boiling point at around 300.3oC at 760 mmHg. The polarity and high reactivity of this chiral auxiliary make it useful in various synthetic applications in the pharmaceutical and fine chemical industries. In addition, it also serves as a resolution agent, meaning it can differentiate between other chiral molecules. Safety measures should be taken while handling as it may cause skin and eye irritation and may be harmful if swallowed or inhaled.

InChI:InChI=1/C12H20O3/c1-8(2)10-5-4-9(3)6-11(10)15-12(14)7-13/h7-11H,4-6H2,1-3H3/t9-,10+,11-/m1/s1

Upstream product

• 21758-30-5 (1R,2S,5R)-(-)-menthyl dichloroacetate 
• 2216-51-5 (-)-menthol 
• 298-12-4 Glyoxilic acid 
• 111969-64-3 L-menthyl glyoxylate monohydrate 
• 81529-62-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-chloro-2-oxoacetate 
• 32815-16-0 Nitrooxy-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 

Downstream Products

• 1027903-28-1 (S)-2-(Benzhydrylidene-amino)-3-phenyl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 147126-62-3 (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester 
• 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 
• 133392-21-9 (2S)-2-hydroxy-2-(2-hydroxy-4-tert-butylphenyl)ethanoic acid (-)-menthyl ester 
• 133392-27-5 (2R)-2-hydroxy-2-(2-hydroxy-4-tert-butylphenyl)ethanoic acid (-)-menthyl ester 
• 85225-31-6 C-[(1R,2S,5R)-menthoxycarbonyl]-N-methylnitrone 
• 141884-00-6 3-Furan-2-yl-2-hydroxy-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 141883-99-0 Hydroxy-(5-methyl-furan-2-yl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 141884-03-9 2-Benzyloxy-3-furan-2-yl-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 141884-01-7 Benzyloxy-(5-methyl-furan-2-yl)-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 1186522-21-3 (R)-(-)-menthyl 2,2-bis(2-hydroxy-6-oxocyclohex-1-enyl)acetate 
• 1187319-46-5 C₂₀H₃₆O₄Si 
• 91604-28-3 (3R,4R)-3-acetyl-1-(di-p-anisylmethyl)-4-(l-menthyloxycarbonyl)-2-azetidinone 

Relevant articles and documents

Method for preparing MGH by reacting sodium aldehydesulfite with MGH esterification liquid

The invention relates to a method for preparing MGH by reacting sodium aldehydesulfite with MGH esterification liquid. MGH is glyoxylic acid L-menthol ester, and the method comprises the following steps: (1) reacting an MGH esterification liquid with sodium acetaldehyde sulfite to obtain an MGH sodium salt solution; (2) reacting the MGH salt solution with acetaldehyde to obtain a mixed system containing an MGH crude product; and (3) separating and purifying the MGH crude product to obtain an MGH fine product and an acetaldehyde sodium sulfite recovery solution. The method is simple in production process, simple and convenient to operate and mild in reaction condition, obviously reduces the generation of wastewater and waste salt, and greatly reduces the investment of distillation wastewater equipment and the cost of solid waste treatment.

Synthetic method for lamivudine

The invention provides a synthetic method for lamivudine. The synthetic method comprises the following steps: cheap easily-available dihaloacetic acid is used as a raw material, the dihaloacetic acidand L-menthol are subjected to condensation, hydrolysis is performed to obtain menthyl glyoxylate, the menthyl glyoxylate and 2,5-dihydroxy-1,4-dithiane are subjected to condensation, halogenation isperformed, the halogenated product and silanized cytosine are subjected to coupling, reduction is performed, the reduced product and salicylic acid are subjected to salt formation to obtain the a salicylate, and finally recrystallization is performed to obtain the optically-pure lamivudine. According to the method provided by the invention, the raw materials used in the whole synthetic process arecheap and easy to obtain, the synthetic process is simple, the synthetic conditions are mild, so that the synthetic costs of the lamivudine are greatly reduced; the raw material utilization rate andreaction selectivity are high, so that the yield of the obtained lamivudine is higher; and at the same time, a chiral substrate is easily removed during the synthesis, three waste (waste water, wastegas and solid waste) generated in the method are less, and the method is suitable for industrialized large-scale production of the lamivudine.

A reduction Suitqable to intermediate MGH synthesis process impurities

The invention discloses a method of reducing impurities in a synthesis process of an emtricitabine intermediate MGH. The method comprises the following steps: taking L-menthol and glyoxylic acid as raw materials; carrying out an esterification reaction under acid catalysis; carrying out an addition reaction under the action of sodium hydrogen sulfite; carrying out a hydroxylation reaction under the action of formaldehyde; carrying out post-treatment to obtain L-menthyl dyhydroxy acetate, wherein in the process of the addition reaction, the pH value is 4-6, and the reaction temperature is 40-80 DEG C and the reaction time is 4-10 hours. With the adoption of the method, the reaction time is greatly shortened and a reaction period is shortened; meanwhile, in a reaction process, cyclohexane is only used as an organic solvent, so that the operation is simple and the post-treatment is convenient; by controlling process conditions and post-treatment conditions, the content of impurities is greatly reduced and the yield is improved. Meanwhile, certain helps are provided for registration and application, and production and center control of emtricitabine, and improvement of quality standards of the emtricitabine intermediate.