WGK Germany | 3 |
methyl 3-oxotetradecanoate
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Stage #1: methyl 3-oxotetradecanoate With hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; ruthenium trichloride In methanol at 40 - 50℃; under 3361.46 Torr; for 20h; Stage #2: With lithium hydroxide In tetrahydrofuran; water | 100% |
With sodium hydroxide; hydrogen; acetic acid; L-Tartaric acid; (R,R)-tartaric acid-NaBr-Raney nickel ((R,R)-TA-NaBr-MRNi); sodium bromide 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: 95.6 percent / H2 / (R)-ruthenium 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / methanol / 5 h / 100 °C / 3750.3 Torr 2: 97.6 percent / lithium hydroxide monohydrate / methanol; H2O / 12 h View Scheme |
methyl (R)-3-hydroxytetradecanoate
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 2h; | 98% |
With lithium hydroxide In methanol; water for 12h; | 97.6% |
With sodium hydroxide In tetrahydrofuran; water Reflux; | 96% |
(R)-1-cyanotridecan-2-ol
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane at 100℃; for 12h; Hydrolysis; | 95% |
(R)-tert-butyl 3-hydroxytetradecanoate
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 0.75h; | 87% |
(R)-3-hydroxytetradecanoic acid ethyl ester
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol | 76% |
With ethanol; potassium hydroxide |
3-hydroxytetradecanoic acid
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With dexamfetamine |
Ethyl 3-hydroxytetradecanoate
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
In diethyl ether (saponification); |
vinyl acetate
3-hydroxytetradecanoic acid
A
(R)-3-hydroxytetradecanoic acid
B
(S)-3-acetoxytetradecanoic acid
Conditions | Yield |
---|---|
With di-tert-butyl-4-methylphenol In tetrahydrofuran at 65℃; for 3h; Pseudomonas lipase; |
3-oxomyristic acid
A
(R)-3-hydroxytetradecanoic acid
B
tridecan-2-one
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 48h; Yield given. Yields of byproduct given; |
(3R)-1-trimethylsilyl-tetradec-1-yn-3-ol
A
(R)-3-hydroxytetradecanoic acid
B
(3S)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; bis(cyclohexanyl)borane; dihydrogen peroxide 1) THF, 0 deg C; 2) 40-50 deg C; Yield given. Multistep reaction. Title compound not separated from byproducts; |
n-dodecanoyl chloride
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridine / CH2Cl2 / 3 h / 0 - 20 °C 1.2: 77.9 percent / methanol / 3 h / Heating 2.1: 95.6 percent / H2 / (R)-ruthenium 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / methanol / 5 h / 100 °C / 3750.3 Torr 3.1: 97.6 percent / lithium hydroxide monohydrate / methanol; H2O / 12 h View Scheme |
1-tridecene
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: K3Fe(CN)6; K2CO3; water / 4,6-bis(9-O-dihydroquinidinyl)-2,5-diphenylpyrimidine; OsO4 / 2-methyl-propan-2-ol; toluene / 24 h / 20 °C 2: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C 3: 86 percent / dimethylformamide / 12 h / 90 °C 4: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme |
(R)-1,2-dihydroxytridecane
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C 2: 86 percent / dimethylformamide / 12 h / 90 °C 3: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme |
(4R)-4-undecyl-1,3,2-dioxathiolane-2-oxide
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / dimethylformamide / 12 h / 90 °C 2: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) CuI / 1.) THF, -30 deg C, 30 min, 2.) THF, a) -30 deg C, 1 h, b) RT, overnight 2: 76 percent / aq. KOH / ethanol View Scheme |
n-dodecanoyl chloride
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: di-t-butyl-p-cresol / tetrahydrofuran / 3 h / 65 °C / Pseudomonas lipase View Scheme |
2,2-dimethyl-4,6-dioxo-5-dodecanoyl-1,3-dioxane
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 5 h / Heating 2: 1.) H2, AcOH, 2.) NaOH / 1.) (R,R)-tartaric acid-NaBr-Raney nickel ((R,R)-TA-NaBr-MRNi) / 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2 View Scheme |
(R)-(-)-1-tetradecyn-3-ol
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 2: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C View Scheme |
tetradec-1-yn-3-one
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.4 eq. R-Alpine-Borane / neat (no solvent) / 8 h / 0 - 20 °C 2: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature 3: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C View Scheme |
1,4-dioxane
methyl (R)-3-hydroxytetradecanoate
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In methanol; water |
n-tetradecanoic acid
A
2-hydroxytetradecanoic acid
B
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With recombinant Bacillus subtilis cytochrome P450(BSβ) F79L mutant; dihydrogen peroxide at 37℃; for 0.0166667h; pH=7; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; regioselective reaction; |
jagaricin
A
D-allo-threonine
B
(2S,3S)-2-amino-3-hydroxybutanoic acid
C
L-threonine
D
D-Glutamin
E
(R)-3-hydroxytetradecanoic acid
F
dehydrobutyrine
G
tyrosine
H
glycine
I
L-histidine
Conditions | Yield |
---|---|
With hydrogenchloride; phenol In water at 105℃; Reagent/catalyst; |
(+/-)-3-hydroxytetradecanoic acid methyl ester
A
(R)-3-hydroxytetradecanoic acid
B
(S)-methyl 3-hydroxymyristate
Conditions | Yield |
---|---|
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; enantioselective reaction; | A n/a B n/a |
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; Resolution of racemate; enantioselective reaction; | A n/a B n/a |
(+/-)-3-hydroxytetradecanoic acid methyl ester
A
(R)-3-hydroxytetradecanoic acid
B
(S)-methyl 3-hydroxymyristate
C
(3S)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; Resolution of racemate; enantioselective reaction; | A n/a B n/a C n/a |
lauric acid
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: magnesium ethylate / 1,4-dioxane 1.2: 20 °C 2.1: hydrogen; dichloro-R-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ruthenium / methanol / 20 h / 50 °C / 3102.97 Torr / Inert atmosphere 3.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 123℃; for 23h; |
1-hydroxy-pyrrolidine-2,5-dione
(R)-3-hydroxytetradecanoic acid
Conditions | Yield |
---|---|
With 2`,3`-dideoxycytidine In tetrahydrofuran for 12h; Ambient temperature; | 100% |
methanol
(R)-3-hydroxytetradecanoic acid
methyl (R)-3-hydroxytetradecanoate
Conditions | Yield |
---|---|
With boron trifluoride at 100℃; for 0.0333333h; | 100% |
With boron trifluoride at 105℃; for 0.75h; |
(R)-3-hydroxytetradecanoic acid
α-bromoacetophenone
(3R)-3-hydroxytetradecanoic acid phenacyl ester
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate | 98% |
With triethylamine In ethyl acetate 1.) 0 deg C, 10 min, 2.) room temp.; | 94% |
With triethylamine In ethyl acetate | 93% |
(R)-3-hydroxytetradecanoic acid
benzyl chloride
3-hydroxy-D-tetradecanoic acid benzyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran; dimethyl sulfoxide at 50℃; | 97% |
(R)-3-hydroxytetradecanoic acid
benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
benzyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside
Conditions | Yield |
---|---|
With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide In dichloromethane | 95% |
With dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature; Yield given; |
(R)-3-hydroxytetradecanoic acid
{(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol
C89H124N2O18
Conditions | Yield |
---|---|
With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 2h; | 88% |
(R)-3-hydroxytetradecanoic acid
triethylsilyl chloride
(R)-3-O-triethylsilyl myristic acid
Conditions | Yield |
---|---|
In pyridine at 60℃; for 2h; | 85.6% |
(R)-3-hydroxytetradecanoic acid
2-(trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
2-(trimethylsilyl)ethyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane Ambient temperature; | 84% |
1-hydroxy-pyrrolidine-2,5-dione
(R)-3-hydroxytetradecanoic acid
N-(R)-3-hydroxytetradecanoyloxysuccinimide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 16h; | 80% |
1H-imidazole
(R)-3-hydroxytetradecanoic acid
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In methanol; dichloromethane; chloroform | 79% |
(R)-3-hydroxytetradecanoic acid
(R)-1,3-dihydroxytetradecane
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 2.5h; Ambient temperature; | 76% |
(R)-3-hydroxytetradecanoic acid
1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride
1,3,4,6-tetra-O-acetyl-2-deoxy-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranose
Conditions | Yield |
---|---|
With triethylamine; dicyclohexyl-carbodiimide In pyridine for 48h; Ambient temperature; | 68% |
(R)-3-hydroxytetradecanoic acid
(S)-methyl 3-(tert-butoxy)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-((2-hydroxyethyl)thio)propanamido)propanoate
methyl (L-(thio-((R)-ethyl 3-hydroxytetradecanoate))-N-(tert-butoxycarbonyl))cysteyl-L-(3-O-(tert-butyl))serate
Conditions | Yield |
---|---|
With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 63% |
(R)-3-hydroxytetradecanoic acid
benzyl bromide
3-hydroxy-D-tetradecanoic acid benzyl ester
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate for 72h; Ambient temperature; | 61% |
With tetra-(n-butyl)ammonium iodide; triethylamine In ethyl acetate at 20℃; for 18h; |
(R)-3-hydroxytetradecanoic acid
Fmoc-Leu-OH
L-Asn(Trt)
Fmoc-L-Gln(Trt)-OH
Conditions | Yield |
---|---|
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 6h; Weinreb amide resin; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.05h; Weinreb amide resin; Stage #3: (R)-3-hydroxytetradecanoic acid; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH Further stages; | 60% |
(R)-3-hydroxytetradecanoic acid
Fmoc-Val-OH
L-Asn(Trt)
Fmoc-L-Gln(Trt)-OH
Conditions | Yield |
---|---|
Stage #1: Fmoc-Val-OH With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 6h; Weinreb amide resin; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.05h; Weinreb amide resin; Stage #3: (R)-3-hydroxytetradecanoic acid; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH Further stages; | 53% |
diazomethane
(R)-3-hydroxytetradecanoic acid
methyl (R)-3-hydroxytetradecanoate
Conditions | Yield |
---|---|
In diethyl ether Yield given; |
methanol
(R)-3-hydroxytetradecanoic acid
A
methyl (R)-3-hydroxytetradecanoate
B
(S)-methyl 3-hydroxymyristate
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Ambient temperature; Yield given. Title compound not separated from byproducts; |
(R)-3-hydroxytetradecanoic acid
Benzyl-6-O-<6-O-acetyl-2-amino-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-β-D-glucopyranosyl>-2-amino-3,4-di-O-<α,α-D2>benzyl-2-desoxy-β-D-glucopyranosid-dihydrochlorid
Benzyl-6-O-<6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3,4-di-O-<α,α-D2>benzyl-2-desoxy-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid
Conditions | Yield |
---|---|
With cyclohexyl(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, 2.) DMF, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With cyclohexyl-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, RT, 2.) DMF, 8 h, RT; Yield given. Multistep reaction; |
(R)-3-hydroxytetradecanoic acid
C34H34(2)H2NO9P*ClH
Benzyl-6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid
Conditions | Yield |
---|---|
With cyclohexyl(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, 2.) DMF, 40 min, RT; Yield given. Multistep reaction; |
(R)-3-hydroxytetradecanoic acid
1,3-di-O-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose hydrochloride
Conditions | Yield |
---|---|
With triethylamine; dicyclohexyl-carbodiimide In pyridine | |
With triethylamine; dicyclohexyl-carbodiimide In pyridine |
Molecular Structure:
Molecular Formula: C14H28O3
Molecular Weight: 244.3703
Systematic Name: (3R)-3-Hydroxytetradecanoic acid
Synonyms of (R)-3-Hydroxymyristic acid (CAS NO.28715-21-1): (3R)-3-Hydroxytetradecanoic acid ; (R)-(-)-3-Hydroxytetradecanoic acid ; (R)-3-Hydroxytetradecanoic acid
CAS NO: 28715-21-1
Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
Melting point: 71-72°C
Index of Refraction: 1.467
Molar Refractivity: 69.96 cm3
Molar Volume: 252.1 cm3
Surface Tension: 37.7 dyne/cm
Density: 0.969 g/cm3
Flash Point: 195.9 °C
Enthalpy of Vaporization: 72.26 kJ/mol
Boiling Point: 376.9 °C at 760 mmHg
Vapour Pressure: 3.16E-07 mmHg at 25°C
(R)-3-Hydroxymyristic acid (CAS NO.28715-21-1) is used as one of two major component of bacterial Lipid A .
WGK Germany of (R)-3-Hydroxymyristic acid (CAS NO.28715-21-1): 3
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