Risk Statements | 10 |
Safety Statements | 16 |
WGK Germany | 3 |
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon | 88% |
diazomethane
(2R)-3-hydroxy-2-methylpropanoic acid
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
In diethyl ether | 86% |
methyl (2R)-3-(benzyloxy)-2-methylpropanoate
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol at 50℃; Industrial scale; | 84% |
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With t-butyl bromide In acetonitrile for 0.833333h; Reflux; chemoselective reaction; | 72% |
methyl 2-hydroxymethylacrylate
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With glucose dehydrogenase; potassium phosphate; D-glucose; ene reductase YqjM wild type enzyme; NADPH In 2-methyltetrahydrofuran; aq. phosphate buffer at 30℃; pH=7.5; Reagent/catalyst; Inert atmosphere; Enzymatic reaction; enantioselective reaction; | 58% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (Rc,Ra)-THNAPhos; hydrogen In dichloromethane at 20℃; under 7500.75 Torr; for 24h; optical yield given as %ee; | |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1-(3-(diphenylphosphanyl)phenyl)urea; (2S)-methyl (S)-2-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-ylamino)-2-isobutylethanoate; hydrogen In dichloromethane at 24.84℃; under 7500.75 Torr; for 16h; |
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
Stage #1: methyl (2R,5S,E)-5-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-3-enoate With ozone In methanol at -78℃; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; | 48% |
diazomethane
3-hydroxyisobutyric acid
A
3-hydroxy-(2S)-methylpropionate
B
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
In diethyl ether Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
methyl 2-hydroxymethylacrylate
A
3-hydroxy-(2S)-methylpropionate
B
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With hydrogen; {(-)-1,2-bis(2R,5R)-2,5-dimethylphospholanobenzene(cyclooctadiene)rhodium(l)} triflate In methanol at 30℃; under 3000.3 Torr; Product distribution; Further Variations:; Catalysts; | |
With hydrogen; Ru(cod)(η3-methylallyl)2/(R)-SYNPHOS/HBF4 In methanol at 50℃; under 15001.5 Torr; for 23h; Title compound not separated from byproducts.; | |
With hydrogen; p-benzoquinone; [RuH(η6-cycloocta-1,3,5-triene)(S)-SYNPHOS]BF4 In methanol at 15℃; under 15001.5 Torr; for 23h; Title compound not separated from byproducts.; |
methyl 3-hydroxy-2-methylpropanoate
A
3-hydroxy-(2S)-methylpropionate
B
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With [Rh(dppb)(COD)]BF4; hydrogen In methanol at 20℃; under 45004.5 Torr; for 20h; | |
With capillary column subsequently coated with 1) Co(d-Cam)1/2(bdc)1/2(tmdpy) (d-Cam=d-camphoric acid,bdc=1,4-benzenedicarboxylic acid, tmdpy=4,4’-trimethylenedipyridine), 2) peramylated β-cyclodextrin at 93℃; Reagent/catalyst; Resolution of racemate; |
3,4-dihydro-2H-pyran
methyl (R)-3-hydroxy-2-methylpropionate
(R)-2-Methyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran Ambient temperature; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; Inert atmosphere; | 100% |
With toluene-4-sulfonic acid In diethyl ether at 20℃; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
tert-butyldimethylsilyl chloride
methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 5℃; Etherification; silylation; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
methyl (R)-3-hydroxy-2-methylpropionate
diphenyldisulfane
(S)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester
Conditions | Yield |
---|---|
With tributylphosphine In acetonitrile for 4.5h; Ambient temperature; | 100% |
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; | 95% |
methyl (R)-3-hydroxy-2-methylpropionate
tert-butylchlorodiphenylsilane
(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane Ambient temperature; | 100% |
With 1H-imidazole In dichloromethane | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Alkylation; | 100% |
methyl (R)-3-hydroxy-2-methylpropionate
O-(4-methoxybenzyl)-trichloroacetimidate
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; | 100% |
With camphor-10-sulfonic acid In dichloromethane for 16h; | 98% |
With camphor-10-sulfonic acid In hexane; dichloromethane at 20℃; for 12h; Inert atmosphere; | 96% |
triisopropylsilyl chloride
methyl (R)-3-hydroxy-2-methylpropionate
methyl (2R)-2-methyl-3-[(1,1,1-triisopropylsilyl)oxy]propanoate
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 72h; silylation; | 100% |
With 1H-imidazole; dmap In dichloromethane at 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
4,4'-dimethoxytrityl chloride
(R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester
Conditions | Yield |
---|---|
With 2,3,5-trimethyl-pyridine In dichloromethane at 25℃; Substitution; | 100% |
With pyridine at 20℃; for 4h; | |
With 2,4,6-trimethyl-pyridine In dichloromethane at 0℃; |
triethylsilyl chloride
methyl (R)-3-hydroxy-2-methylpropionate
methyl (R)-2-methyl-3-(triethylsilyl)oxypropanoate
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With 1H-imidazole; dmap | 99% |
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 4h; | |
With 1H-imidazole Inert atmosphere; |
methyl (R)-3-hydroxy-2-methylpropionate
trityl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With dmap; triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere; Cooling with ice; | 90% |
With dmap; triethylamine In dichloromethane at 20℃; | 63% |
methyl (R)-3-hydroxy-2-methylpropionate
Trichloroacetyl isocyanate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 100% |
In dichloromethane at 20℃; for 1h; |
methyl (R)-3-hydroxy-2-methylpropionate
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction; | 100% |
methyl (R)-3-hydroxy-2-methylpropionate
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In diethyl ether at 20℃; for 18h; Inert atmosphere; | 100% |
3,4-dihydro-2H-pyran
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In diethyl ether Ambient temperature; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
methylmagnesium bromide
(R)-2,3-dimethyl-1,3-butanediol
Conditions | Yield |
---|---|
In diethyl ether at 0 - 25℃; for 1.5h; | 99% |
In tetrahydrofuran at -10℃; for 3h; Grignard Reaction; Inert atmosphere; | 77% |
In diethyl ether at 0 - 20℃; for 3h; | 72% |
In tetrahydrofuran; diethyl ether | 57% |
In tetrahydrofuran; diethyl ether at 0℃; for 2h; | 57% |
methyl (R)-3-hydroxy-2-methylpropionate
chloromethyl methyl ether
(R)-(-)-methyl 3-(methoxymethoxy)-2-methylpropionate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature; | 99% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature; | 99% |
With diisopropylamine In dichloromethane for 16h; Ambient temperature; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
p-toluenesulfonyl chloride
methyl (R)-2-methyl-3-[(4'-toluenesulfonyl)oxy]propionate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 1h; | 99% |
With dmap; triethylamine In dichloromethane at 20℃; for 12h; Cooling with ice; | 98% |
With triethylamine In dichloromethane at 20℃; for 12h; | 98% |
methyl (R)-3-hydroxy-2-methylpropionate
acetic anhydride
Methyl (R)(-)-3-acetoxy-2-methylpropanoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With 2,6-di-tert-butylpyridin-1-ium trifluoromethanesulfonate In 1,4-dioxane at 20℃; for 4h; Molecular sieve; | 99% |
methyl (R)-3-hydroxy-2-methylpropionate
ethyl vinyl ether
methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 4h; Ambient temperature; | 98.1% |
With toluene-4-sulfonic acid In diethyl ether at 20℃; for 2h; | 93% |
With pyridinium p-toluenesulfonate In dichloromethane for 0.25h; Ambient temperature; | |
With pyridinium p-toluenesulfonate | |
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; |
methyl (R)-3-hydroxy-2-methylpropionate
3,4-dimethoxybenzyl 2,2,3,3,3-pentafluoropropionimidate
methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1h; | 98% |
methyl (R)-3-hydroxy-2-methylpropionate
1-Phenyl-1H-tetrazole-5-thiol
(2S)-methyl-3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)propionic acid methyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 5h; | 98% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; | 98% |
methyl (R)-3-hydroxy-2-methylpropionate
methyl (2R)-3-(benzyloxy)-2-methylpropanoate
Conditions | Yield |
---|---|
In α,α,α-trifluorotoluene at 120℃; for 0.333333h; Microwave irradiation; | 98% |
With magnesium oxide In α,α,α-trifluorotoluene at 80℃; for 24h; | 85% |
With magnesium oxide at 83℃; for 24h; Inert atmosphere; | 82% |
With magnesium oxide In 1,2-dichloro-ethane Heating; | 72% |
Benzyloxymethyl chloride
methyl (R)-3-hydroxy-2-methylpropionate
(2R)-3-benzyloxymethoxy-2-methylpropionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Benzyloxymethyl chloride; methyl (R)-3-hydroxy-2-methylpropionate With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 16h; Stage #2: With tetra-(n-butyl)ammonium iodide In dichloromethane at 20℃; for 3h; | 97% |
Stage #1: Benzyloxymethyl chloride; methyl (R)-3-hydroxy-2-methylpropionate With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; Stage #2: With tetra-(n-butyl)ammonium iodide at 20℃; for 3h; | 97% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 44h; Ambient temperature; |
methyl (R)-3-hydroxy-2-methylpropionate
methyl (S)-3-iodo-2-methylpropanoate
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 0 - 20℃; for 2.5h; | 97% |
Stage #1: methyl (R)-3-hydroxy-2-methylpropionate With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane at 0 - 20℃; for 2.5h; Stage #2: With sodium iodide In acetonitrile at 70℃; for 16h; | 72% |
1.) tosylation; 2.) iodination; Multistep reaction; |
methyl (R)-3-hydroxy-2-methylpropionate
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With lanthanum(lll) triflate In toluene at 0 - 20℃; for 16h; Inert atmosphere; | 97% |
(R)-3,4-dihydro-2H-benzo[b][1,4]oxathiepin-3-amine
methyl (R)-3-hydroxy-2-methylpropionate
N-[3,4-dihydro-1,5-benzoxathiepin-3-yl]-(R)-(3-hydroxy-2-(R)-methyl)propionamide
Conditions | Yield |
---|---|
Stage #1: (R)-3,4-dihydro-2H-benzo[b][1,4]oxathiepin-3-amine With diisobutylaluminium hydride In tetrahydrofuran at 10 - 20℃; Inert atmosphere; Stage #2: methyl (R)-3-hydroxy-2-methylpropionate In tetrahydrofuran at -10 - 50℃; Stage #3: With water; Rochelle's salt In tetrahydrofuran for 2h; Inert atmosphere; | 96.8% |
methyl (R)-3-hydroxy-2-methylpropionate
methyl (2R)-3-(benzyloxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With magnesium oxide In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere; | 96% |
methyl (R)-3-hydroxy-2-methylpropionate
O-benzyl 2,2,2-trichloroacetimidate
methyl (2R)-3-(benzyloxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 95% |
With trifluorormethanesulfonic acid In dichloromethane at 0℃; | 91% |
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 20℃; for 3h; | 88% |
methyl (R)-3-hydroxy-2-methylpropionate
3,4-dimethoxybenzyl 2,2,3,3,4,4,4-heptafluorobutyrimidate
methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1h; | 95% |
methyl (R)-3-hydroxy-2-methylpropionate
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,4-dioxane at 50℃; for 4h; Molecular sieve; | 95% |
Molecular structure of Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) is:
Product Name: Methyl (R)-(-)-3-hydroxy-2-methylpropionate
CAS Registry Number: 72657-23-9
IUPAC Name: methyl 3-Hydroxy-2-methylpropanoate
Molecular Weight: 118.1311 [g/mol]
Molecular Formula: C5H10O3
XLogP3-AA: -0.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Refractive index: n20/D 1.425
Storage temp.: 2-8 °C
Surface Tension: 33.218 dyne/cm
Density: 1.051 g/cm3
Flash Point: 81.111 °C
Enthalpy of Vaporization: 47.893 kJ/mol
Boiling Point: 175.048 °C at 760 mmHg
Vapour Pressure: 0.361 mmHg at 25 °C
Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) can be used in chiral derivative of 3-Hydroxyisobutyrate.
Safty information about Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) is:
Risk Statements: 10
R10:Flammable.
Safety Statements: 16
S16:Keep away from sources of ignition.
WGK Germany: 3
Methyl (R)-(-)-3-hydroxy-2-methylpropionate , its cas register number is 72657-23-9. It also can be called Propanoic acid,3-hydroxy-2-methyl-, methyl ester, (2R)- ; (-)-Methyl D-beta-hydroxyisobutyrate .It is a clear colorless oil.
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