28715-21-1

Basic information

• Product Name: 3-HYDROXYTETRADECANOIC ACID
• Synonyms: DL-BETA-HYDROXYMYRISTIC ACID;HYDROXYMYRISTIC ACID, 3-;(+/-)-3-HYDROXYTETRADECANOIC ACID;3-HYDROXYTETRADECANOIC ACID;3-HYDROXY C14:0 ACID;3-HYDROXYMYRISTIC ACID;3-HYDROXYMYRISTIC ACID (BETA-);(R)-(-)-3-Hydroxytetradecanoic
• CAS NO: 28715-21-1
• Molecular Formula: C₁₄H₂₈O₃
• Molecular Weight: 244.37
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 28715-21-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 71-72°C
• Boiling Point: 376.9°C at 760 mmHg
• Flash Point: 195.9°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 3.16E-07mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Diethyl Ether (Slightly), Eth
• PKA: 4.38±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXYTETRADECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYTETRADECANOIC ACID(28715-21-1)
• EPA Substance Registry System: 3-HYDROXYTETRADECANOIC ACID(28715-21-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 28715-21-1(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

One of two major component of bacterial Lipid A .

Definition

ChEBI: A 3-hydroxytetradecanoic acid that has R configuration at position 3. It plays an intermediate role in fatty acid biosynthesis.

InChI:InChI=1/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1

Synthetic route

methyl 3-oxotetradecanoate (22348-97-6) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (76062-97-0) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (259799-90-1) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With hydrogenchloride In dichloromethane at 100℃; for 12h; Hydrolysis;	95%

(R)-tert-butyl 3-hydroxytetradecanoate (79816-65-2) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 0.75h;	87%

(R)-3-hydroxytetradecanoic acid ethyl ester (151763-75-6) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With potassium hydroxide In ethanol	76%
With ethanol; potassium hydroxide

3-hydroxytetradecanoic acid (1961-72-4) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With dexamfetamine

Ethyl 3-hydroxytetradecanoate (126679-29-6) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
In diethyl ether (saponification);

vinyl acetate (108-05-4) + 3-hydroxytetradecanoic acid (1961-72-4) → (R)-3-hydroxytetradecanoic acid (28715-21-1) + (S)-3-acetoxytetradecanoic acid (151378-83-5)

Conditions	Yield
With di-tert-butyl-4-methylphenol In tetrahydrofuran at 65℃; for 3h; Pseudomonas lipase;

3-oxomyristic acid (88222-72-4) → (R)-3-hydroxytetradecanoic acid (28715-21-1) + tridecan-2-one (593-08-8)

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 (74794-26-6) → (R)-3-hydroxytetradecanoic acid (28715-21-1) + (3S)-3-hydroxytetradecanoic acid (35683-15-9)

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 (112-16-3) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (2437-56-1) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (96883-16-8) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (259799-88-7) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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

n-decyl magnesium bromide (17049-50-2) + HgBr2 → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (112-16-3) + alcoholic NaOH → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (111861-21-3) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (77889-04-4, 136022-04-3, 73501-38-9) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (73501-40-3) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (123-91-1) + methyl (R)-3-hydroxytetradecanoate (76062-97-0) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol; water

n-tetradecanoic acid (544-63-8) → 2-hydroxytetradecanoic acid (2507-55-3) + (R)-3-hydroxytetradecanoic acid (28715-21-1)

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 (1422729-34-7) → D-allo-threonine (24830-94-2) + (2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3) + L-threonine (72-19-5) + D-Glutamin (5959-95-5) + (R)-3-hydroxytetradecanoic acid (28715-21-1) + dehydrobutyrine (20748-08-7) + tyrosine (556-02-5) + glycine (56-40-6) + L-histidine (71-00-1)

Conditions	Yield
With hydrogenchloride; phenol In water at 105℃; Reagent/catalyst;

...Expand

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (R)-3-hydroxytetradecanoic acid (28715-21-1) + (S)-methyl 3-hydroxymyristate (76835-67-1)

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 (55682-83-2) → (R)-3-hydroxytetradecanoic acid (28715-21-1) + (S)-methyl 3-hydroxymyristate (76835-67-1) + (3S)-3-hydroxytetradecanoic acid (35683-15-9)

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 (143-07-7) → (R)-3-hydroxytetradecanoic acid (28715-21-1)

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

C37H66N4O8 → L-leucine (61-90-5) + L-glutamic acid (56-86-0) + (R)-3-hydroxytetradecanoic acid (28715-21-1)

Conditions	Yield
With hydrogenchloride In water at 123℃; for 23h;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (R)-3-hydroxytetradecanoic acid (28715-21-1) → N-<(R)-3-hydroxytetradecanoyloxy>succinimide

Conditions	Yield
With 2`,3`-dideoxycytidine In tetrahydrofuran for 12h; Ambient temperature;	100%

methanol (67-56-1) + (R)-3-hydroxytetradecanoic acid (28715-21-1) → methyl (R)-3-hydroxytetradecanoate (76062-97-0)

Conditions	Yield
With boron trifluoride at 100℃; for 0.0333333h;	100%
With boron trifluoride at 105℃; for 0.75h;

(R)-3-hydroxytetradecanoic acid (28715-21-1) + α-bromoacetophenone (70-11-1) → (3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1)

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 (28715-21-1) + benzyl chloride (100-44-7) → 3-hydroxy-D-tetradecanoic acid benzyl ester (88862-84-4)

Conditions	Yield
In tetrahydrofuran; dimethyl sulfoxide at 50℃;	97%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (102794-17-2) → benzyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (104640-20-2)

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 (28715-21-1) + {(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 (96961-24-9) → C89H124N2O18 (96961-25-0)

Conditions	Yield
With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 2h;	88%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + triethylsilyl chloride (994-30-9) → (R)-3-O-triethylsilyl myristic acid (915406-25-6)

Conditions	Yield
In pyridine at 60℃; for 2h;	85.6%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + 2-(trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (122078-72-2) → 2-(trimethylsilyl)ethyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside (122078-73-3)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane Ambient temperature;	84%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (R)-3-hydroxytetradecanoic acid (28715-21-1) → N-(R)-3-hydroxytetradecanoyloxysuccinimide (33796-65-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 16h;	80%

1H-imidazole (288-32-4) + (R)-3-hydroxytetradecanoic acid (28715-21-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-3-t-Butyldimethyl-Silyloxytetradecanoic Acid

Conditions	Yield
In methanol; dichloromethane; chloroform	79%

(R)-3-hydroxytetradecanoic acid (28715-21-1) → (R)-1,3-dihydroxytetradecane (139623-13-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 2.5h; Ambient temperature;	76%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4) → 1,3,4,6-tetra-O-acetyl-2-deoxy-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranose (74660-52-9, 77448-50-1, 121700-61-6)

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide In pyridine for 48h; Ambient temperature;	68%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + (S)-methyl 3-(tert-butoxy)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-((2-hydroxyethyl)thio)propanamido)propanoate (1346422-43-2) → methyl (L-(thio-((R)-ethyl 3-hydroxytetradecanoate))-N-(tert-butoxycarbonyl))cysteyl-L-(3-O-(tert-butyl))serate (1620278-76-3)

Conditions	Yield
With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	63%

(R)-3-hydroxytetradecanoic acid (28715-21-1) + benzyl bromide (100-39-0) → 3-hydroxy-D-tetradecanoic acid benzyl ester (88862-84-4)

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 (28715-21-1) + Fmoc-Leu-OH (35661-60-0) + L-Asn(Trt) (132388-59-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1) → deoxy-fellutamide D

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 (28715-21-1) + Fmoc-Val-OH (68858-20-8) + L-Asn(Trt) (132388-59-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1) → deoxy-fellutamide C

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 (186581-53-3, 908094-01-9) + (R)-3-hydroxytetradecanoic acid (28715-21-1) → methyl (R)-3-hydroxytetradecanoate (76062-97-0)

Conditions	Yield
In diethyl ether Yield given;

methanol (67-56-1) + (R)-3-hydroxytetradecanoic acid (28715-21-1) → methyl (R)-3-hydroxytetradecanoate (76062-97-0) + (S)-methyl 3-hydroxymyristate (76835-67-1)

Conditions	Yield
With hydrogenchloride for 2h; Ambient temperature; Yield given. Title compound not separated from byproducts;

(R)-3-hydroxytetradecanoic acid (28715-21-1) + 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 (106115-93-9) → 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 (106115-95-1)

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;

(R)-3-hydroxytetradecanoic acid (28715-21-1) + Benzyl-O- (106115-86-0) → C85H116(2)H6N2O24 (106115-87-1)

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 (28715-21-1) + C34H34(2)H2NO9P*ClH (106139-09-7) → Benzyl-6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid (106115-91-7)

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 (28715-21-1) + 1,3-di-O-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose hydrochloride (85065-28-7) → Acetic acid (4aR,6S,7R,8R,8aS)-6-acetoxy-7-((R)-3-hydroxy-tetradecanoylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide In pyridine
With triethylamine; dicyclohexyl-carbodiimide In pyridine

Upstream product

• 123-91-1 1,4-dioxane 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 1961-72-4 3-hydroxytetradecanoic acid 
• 544-63-8 n-tetradecanoic acid 
• 143-07-7 lauric acid 
• 79816-65-2 tert-butyl (R)-3-hydroxytetradecanoate 
• 55682-83-2 (+/-)-3-hydroxytetradecanoic acid methyl ester 
• 1422729-34-7 jagaricin 
• 73501-40-3 tetradec-1-yn-3-one 
• 77889-04-4 (R)-(-)-1-tetradecyn-3-ol 
• 111861-21-3 2,2-dimethyl-4,6-dioxo-5-dodecanoyl-1,3-dioxane 
• 112-16-3 n-dodecanoyl chloride 
• 17049-50-2 n-decyl magnesium bromide 
• 259799-88-7 (4R)-4-undecyl-1,3,2-dioxathiolane-2-oxide 

Downstream Products

• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 76835-67-1 (S)-methyl 3-hydroxymyristate 
• 88862-84-4 3-hydroxy-D-tetradecanoic acid benzyl ester 
• 92949-55-8 allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside 
• 114360-80-4 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 92949-56-9 allyl 4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-6-O-<2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranoside 
• 118638-59-8 1-O-acetyl-2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-D-glucopyranose 
• 137600-37-4 allyl 2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl>-α-D-glucopyranoside 
• 137600-40-9 (R)-3-(2,2,2-Trichloro-ethoxycarbonyloxy)-tetradecanoic acid (2R,3R,4R,5S,6R)-2-bromo-5-(diphenoxy-phosphoryloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-6-(2,2,2-trichloro-ethoxycarbonyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 132791-96-9 allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4-O-diphenylphosphono-α-D-glucopyranoside 
• 139623-11-3 4,6-O-<(R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranosyl dibenzyl phosphate 
• 132828-14-9 2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl dibenzyl phosphate 
• 132791-95-8 allyl 6-O-benzyloxymethyl-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside 
• 139623-09-9 Allyl 4,6-O-<(3R)-benzylidene>-2-<(3R)-3-(benzyloxy)tetradecanamido>-3-O-<(3R)-3-(benzyloxy)tetradecanyl>-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

Enantioselective synthesis of 3-hydroxytetradecanoic acid and its methyl ester enantiomers as new antioxidants and enzyme inhibitors

Optically pure R and S enantiomers of 3-hydroxytetradecanoic acid and its methyl esters were synthesised by porcine pancreas lipase catalysed hydrolysis of racemic methyl 3-hydroxytetradecanoate in aqueous medium, with the aim of determining their antioxidant, antielastase and antiurease activities. The effects of the weight ratio of substrate/lipase and the reaction time were investigated. Optimum reaction conditions were determined. The resolution reaction with porcine pancreas lipase afforded (R)-3-hydroxytetradecanoic acid, which is a component of bacterially important lipid A, with greater than 99 % ee in excellent enantiomeric ratio (>900) after 7 h incubation with a substrate/lipase weight ratio of 3:1 and 43 % conversion of the substrate. Methyl (S)-3-hydroxytetradecanoate, which is the unreacted enantiomer of the racemic substrate, could be recovered with 98 % ee after 7 h resolution with a substrate/lipase weight ratio of 1:1 and 60 % conversion. (R)-3- Hydroxytetradecanoic acid was converted to its ester and the S methyl ester to its acid. This biocatalytic enantioselective resolution in aqueous medium presents an environmentally friendly and green chemistry method for the synthesis of R and S enantiomers of 3-hydroxytetradecanoic acid and its methyl esters.

Synthesis of monophosphoryl lipid A using 2-naphtylmethyl ethers as permanent protecting groups

Lipid A, which is a conserved component of lipopolysaccharides of gram-negative bacteria, has attracted considerable interest for the development of immuno-adjuvants. Most approaches for lipid A synthesis rely on the use of benzyl ethers as permanent protecting groups. Due to the amphiphilic character of lipid A, these compounds aggregate during the hydrogenation step to remove benzyl ethers, resulting in a sluggish reaction and by-product formation. To address this problem, we have developed a synthetic approach based on the use of 2-naphtylmethyl ether (Nap) ethers as permanent protecting group for hydroxyls. At the end of a synthetic sequence, multiple of these protecting groups can readily be removed by oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). Di-allyl N,N-diisopropylphosphoramidite was employed to install the phosphate ester and the resulting allyl esters were cleaved using palladium tetrakistriphenylphosphine. The synthetic strategy allows late stage introduction of different fatty acids at the amines of the target compound, which is facilitated by Troc and Fmoc as orthogonal amino-protecting groups.

SYNTHETIC GLUCOPYRANOSYL LIPID ADJUVANTS

PROBLEM TO BE SOLVED: To provide a novel glucopyranosyl lipid adjuvant (GLA) for inducing or enhancing immune responses, and a vaccine composition and a pharmaceutical composition comprising the GLA. SOLUTION: The present invention provides a GLA represented by a compound of the following formula, and a vaccine composition and a pharmaceutical composition comprising the GLA. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT