111969-64-3

Basic information

• Product Name: (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl dihydroxy-acetate
• Synonyms: (1S)-(+)-MENTHYL GLYOXYLATE HYDRATE;Glyoxylic acid (1S)-menthyl ester hydrate;L)-Menthyl glyoxylate monohydrate;(S)-(+)-MENTHYL GLYOXYLATE HYDRATE;(1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl dihydroxy-acetate;2,2-Dihydroxyacetic acid (-)-menthyl ester;L-Menthyl glyoxylate hydrate;L-MGH
• CAS NO: 111969-64-3
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.3
• EINECS: 416-810-6
• Mol File: 111969-64-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 76-78°C
• Boiling Point: 320°C
• Flash Point: 113°C
• Appearance: /
• Density: 1.09
• Vapor Pressure: 2.74E-05mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 10.79±0.41(Predicted)
• Water Solubility: 400g/L
• Sensitive: Air Sensitive
• BRN: 4905777
• CAS DataBase Reference: (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl dihydroxy-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl dihydroxy-acetate(111969-64-3)
• EPA Substance Registry System: (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexyl dihydroxy-acetate(111969-64-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 51/53-48/22-41
• Safety Statements: 61-36/39-26-22
• RIDADR: 3077
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 111969-64-3(Hazardous Substances Data)

Usage

Chemical Properties

Class white particles

Uses

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.

InChI:InChI=1/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-/m0/s1

Synthetic route

C12H21O6S(1-)*Na(1+) → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With formaldehyd; water In cyclohexane at 25℃; for 4h; pH=6.7 - 7.7;	86%

C12H21O6S(1-)*Na(1+) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)acetate + L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With formaldehyd; water In cyclohexane at 20℃; for 16h; pH=6.7 - 7.7;	A 10% B 70%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-chloro-2-oxoacetate (81529-62-6) → L-menthyl glyoxylate (26315-61-7) + L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) 1.) PhH, r.t., 2 h, 2.) PhH, CH2Cl2, reflux, 1 h; Title compound not separated from byproducts;

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-chloro-2-oxoacetate (81529-62-6) → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With water; tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) 1.) PhH, r.t., 2 h; PhH, CH2Cl2, reflux, 1 h; Multistep reaction;

(-)-menthol (2216-51-5) + l-α.α'-diphenyl-succinic acid → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3 / 2 h / Ambient temperature 2: Bu3SnH / Pd(Ph3P)4 / 1.) PhH, r.t., 2 h, 2.) PhH, CH2Cl2, reflux, 1 h View Scheme
Multi-step reaction with 2 steps 1: CHCl3 / 2 h / Ambient temperature 2: 1.) Bu3SnH, 2.) H2O / 1.) Pd(Ph3P)4 / 1.) PhH, r.t., 2 h; PhH, CH2Cl2, reflux, 1 h View Scheme

(-)-menthol (2216-51-5) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2,2-bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)acetate + L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / cyclohexane / 5 h / Reflux 2: sodium hydrogensulfite / cyclohexane; water / 8 h / 25 - 30 °C / pH 4.5 - 5.5 3: formaldehyd; water / cyclohexane / 16 h / 20 °C / pH 6.7 - 7.7 View Scheme

(-)-menthol (2216-51-5) → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / cyclohexane / 5 h / Reflux 2: sodium hydrogensulfite / cyclohexane; water / 8 h / 25 - 30 °C / pH 4.5 - 5.5 3: formaldehyd; water / cyclohexane / 4 h / 25 °C / pH 6.7 - 7.7 View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / cyclohexane / 4 h / 79 - 80 °C 2: sodium hydrogensulfite; sodium carbonate / water / 1.5 h / 50 °C / pH 4.7 - 5.4 3: water; formaldehyd; sodium carbonate / 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / cyclohexane / Reflux 2: sodium carbonate / -75 - 80 °C / pH 4 - 5 3: acetaldehyde / cyclohexane / 2.5 h / 0 - 40 °C View Scheme

L-menthyl glyoxylate (26315-61-7) → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogensulfite / cyclohexane; water / 8 h / 25 - 30 °C / pH 4.5 - 5.5 2: formaldehyd; water / cyclohexane / 4 h / 25 °C / pH 6.7 - 7.7 View Scheme

C12H21O6S(1-)*Na(1+) → L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With formaldehyd; water; sodium carbonate at 20℃; for 0.5h;

C12H21O6S(1-)*Na(1+) → L-menthol glyoxylate monohydrate (111969-64-3) + potassium 1-hydroxyethane-1-sulfonate (918-04-7)

Conditions	Yield
With acetaldehyde In cyclohexane at 0 - 40℃; for 2.5h;

C12H21O6S(1-)*Na(1+) → Reaxys ID: 37256322 + L-menthol glyoxylate monohydrate (111969-64-3)

(-)-menthol (2216-51-5) + Glyoxilic acid (298-12-4) → bis[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxalate (2085-26-9) + L-menthol glyoxylate monohydrate (111969-64-3)

Conditions	Yield
With Amberlyst-15 In acetonitrile at 120℃; under 7500.75 Torr; Reagent/catalyst; Microwave irradiation;

1,4-dithiane-2,5-diol (40018-26-6) + L-menthol glyoxylate monohydrate (111969-64-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate (200396-19-6)

Conditions	Yield
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 110 - 115℃; Stage #2: 1,4-dithiane-2,5-diol In toluene Heating;	100%
Stage #1: 1,4-dithiane-2,5-diol With acetic acid In acetonitrile at 40 - 45℃; for 0.166667h; Stage #2: L-menthyl glyoxylate monohydrate In acetonitrile at 90℃; for 0.166667h;	88%
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 110 - 111℃; for 3h; Stage #2: 1,4-dithiane-2,5-diol In toluene at 85 - 90℃; for 2h; Stage #3: With triethylamine In n-heptane at 0 - 5℃; for 6h;	80%
Stage #1: L-menthyl glyoxylate monohydrate With acetic acid In toluene at 120℃; for 2h; Dean-Stark; Stage #2: 1,4-dithiane-2,5-diol In toluene for 4h; Reflux; Stage #3: With triethylamine In hexane; toluene at 0℃; for 16h;

1,4-dithiane-2,5-diol (40018-26-6) + L-menthol glyoxylate monohydrate (111969-64-3) → (2R,5R)-5-hydroxy-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-isopropylcyclohexyl ester (147126-62-3)

Conditions	Yield
With acetic acid In acetone at 50 - 125℃; Temperature; Solvent;	88%
Stage #1: 1,4-dithiane-2,5-diol; L-menthyl glyoxylate monohydrate In toluene Stage #2: With triethylamine In hexane; toluene	80%
With acetic acid In toluene at 50 - 115℃;	100 g

trimethylsilyl cyanide (7677-24-9) + L-menthol glyoxylate monohydrate (111969-64-3) → Cyano-hydroxy-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions	Yield
With ytterbium(III) triflate In dichloromethane for 2h; Ambient temperature;	82%

L-menthol glyoxylate monohydrate (111969-64-3) + N-benzyl hydroxylalmine (622-30-0) → C19H27NO3 (85252-42-2, 112020-51-6)

Conditions	Yield
In benzene for 1.5h; Heating;	80.7%

L-menthol glyoxylate monohydrate (111969-64-3) + allyl-trimethyl-silane (762-72-1) → 2-Hydroxy-pent-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions	Yield
With methanesulfonic acid In dichloromethane at 25℃; for 15h; Hosomi-Sakurai reaction;	72%

p,p'-dimethoxybenzhydrylamine (19293-62-0) + L-menthol glyoxylate monohydrate (111969-64-3) → [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (91538-20-4)

Conditions	Yield
In toluene Heating;

L-menthol glyoxylate monohydrate (111969-64-3) → L-menthyl glyoxylate (26315-61-7)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 4h; Heating;

L-menthol glyoxylate monohydrate (111969-64-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carbaxylate (147027-10-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene 1.2: 80 percent / Et3N / toluene; hexane 2.1: SOCl2 / dimethylformamide; CH2Cl2 View Scheme
Multi-step reaction with 4 steps 1.1: acetic acid / acetonitrile / 0.17 h / 40 - 45 °C 1.2: 0.17 h / 90 °C 2.1: pyridine / acetonitrile / 20 °C 2.2: 0.08 h / 20 °C 3.1: triethylamine / hexane / 36 h / -20 °C 4.1: pyridinium triflate / acetonitrile / 0.14 h / 80 °C / 517.16 Torr / Flow reactor View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid / acetone / 50 - 125 °C 2.1: pyridine / acetone; dichloromethane / 20 °C 2.2: 24 h / -10 °C 3.1: acetonitrile / 0.17 h 3.2: 2 h / 80 °C View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene 1.2: 80 percent / Et3N / toluene; hexane 2.1: SOCl2 / dimethylformamide; CH2Cl2 View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → 5S-chloro-[1,3]oxathiolane-2R-carboxilic acid 2-(1'R,2'S,5'R)-isopropyl-5-methyl-cyclohexyl ester (288325-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene 1.2: 80 percent / Et3N / toluene; hexane 2.1: SOCl2 / dimethylformamide; CH2Cl2 View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4R)-3-<(R)-1'-hydroxyethyl>-4-(-)menthyloxycarbonyl-1-dimethyl-t-butylsilylazetidin-2-one (115831-80-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 50 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C 5: 23 percent / triethylamine / dimethylformamide / 24 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions	Yield
Multi-step reaction with 6 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 50 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C 5: 56 percent / triethylamine / dimethylformamide / 24 h / Ambient temperature 6: 48 percent / aqueous sodium hydroxide / tetrahydrofuran; methanol / 8 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4S)-3-<(R)-1'-hydroxyethyl>-4-(-)-menthyloxycarbonylazetidin-2-one (111969-66-5, 115936-62-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: 30 percent / benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 20 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4R)-3-<(R)-1'-hydroxyethyl>-4-(-)-menthyloxycarbonylazetidin-2-one (111969-66-5, 115936-62-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 50 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (2S,3S)-2-Amino-3-((R)-1-hydroxy-ethyl)-succinic acid 1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: 30 percent / benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 20 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (2R,3S)-2-Amino-3-((R)-1-hydroxy-ethyl)-succinic acid 1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 50 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4S)-4-(-)-menthyloxycarbonyl-1-dimethyl-t-butylsilyl-3-<(R)-1-(dimethyl-t-butylsilyloxy)ethyl>azetidin-2-one (111969-67-6, 115936-63-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: 30 percent / benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 20 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C 5: 80 percent / triethylamine / dimethylformamide / 16 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-(-)-menthyloxycarbonyl-1-dimethyl-t-butylsilylazetidin-2-one (111969-67-6, 115936-63-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating 3: H2 / platinum oxide / methanol / 50 h / Ambient temperature 4: DCC / acetonitrile / 3 h / 60 °C 5: 56 percent / triethylamine / dimethylformamide / 24 h / Ambient temperature View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3R,4S,5R)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine (115936-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4S,5R)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine (111969-65-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: 30 percent / benzene / 5 h / Heating View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (3S,4R,5S)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine (111969-65-4, 115936-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80.7 percent / benzene / 1.5 h / Heating 2: benzene / 5 h / Heating View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (2S,3S)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (86207-20-7, 86258-95-9, 98759-25-2, 98759-26-3, 137765-45-8, 137765-46-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Heating View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → (2R,3R)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (98759-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / Heating View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate (1346921-53-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid / toluene / 110 - 115 °C 1.2: Heating 2.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 5 - 30 °C 3.1: chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane / dichloromethane / 110 - 120 °C 3.2: 30 - 35 °C View Scheme

L-menthol glyoxylate monohydrate (111969-64-3) → C14H23ClO3S (1346921-70-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / toluene / 110 - 115 °C 1.2: Heating 2.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 5 - 30 °C View Scheme

Upstream product

• 2216-51-5 (-)-menthol 
• 298-12-4 Glyoxilic acid 
• 26315-61-7 L-menthyl glyoxylate 
• 81529-62-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-chloro-2-oxoacetate 
• 86287-64-1 (2E,1'S,2'R,5'S)-but-2-enedioic acid bis(2'-isopropyl-5'methyl-cyclohexyl) ester 
• 124600-69-7 bis[(1S,2R,5S)-2-isopropyl-5-methylcyclohex-1-yl] (R,R)-tartrate 

Downstream Products

• 147126-67-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate 
• 147126-78-1 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[4-(methylcarboxamido)-2-oxo-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate 
• 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 
• 147126-73-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 
• 147126-65-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 147027-09-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate 
• 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 
• 98759-26-3 (2R,3R)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 137765-46-9 (2R,3R)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 137765-45-8 (3S,4S)-1-(di-p-anisylmethyl)-3-ethenyl-4-(d-menthyloxycarbonyl)-2-azetidinone 
• 111969-65-4 (3S,4R,5S)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine 
• 111969-65-4 (3S,4S,5R)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine 
• 115936-61-3 (3R,4S,5R)-2-benzyl-4-benzyloxycarbonyl-3-(-)-menthyloxycarbonyl-5-methylisoxazolidine 
• 111969-67-6 (3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-(-)-menthyloxycarbonyl-1-dimethyl-t-butylsilylazetidin-2-one 

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.

Method for continuous production of L-menthol-dihydroxy acetate

The invention provides a method for continuous production of L-menthol-dihydroxy acetate. The method comprises the steps: (1) subjecting menthol to a reaction with glyoxylic acid in an inert solvent in the presence of a catalyst, so as to obtain an esterification solution; (2) mixing the esterification solution with sodium bisulfite, and carrying out an addition reaction, so as to obtain an addition reaction solution; and (3) mixing the addition reaction solution with formaldehyde, and carrying out a reduction reaction, thereby preparing a compound represented by a formula MGH. According to the method provided by the invention, continuous production can be achieved, side reactions are effectively controlled, the reaction selectivity and raw material utilization ratio are increased, the treatment capacity of wastewater is reduced, and the unit-volume productivity of equipment is improved, so that the method is applicable to industrial large-scale production.

An efficient method for preparation of chiral arylmenthol glyoxylates

Glyoxylates of three chiral alcohols were conveniently prepared by reaction of the alcohol with oxalyl chloride followed by reduction of the resulting alkoxy oxalyl chloride with tributyl- tin hydride. The products were isolated in 75-80% yield by straightforward flash chromatography.