Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 40h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
Stage #1: 1-α-glycerophosphocholine cadmium chloride salt; 1-hexadecylcarboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: In dichloromethane | 83% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 72h; Steglich Esterification; |
L-glycero-3-phosphorylcholine
1-hexadecylcarboxylic acid
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With dmap; Hyflo Supre-Cel; dicyclohexyl-carbodiimide In chloroform at 30℃; | 80% |
Stage #1: L-glycero-3-phosphorylcholine; 1-hexadecylcarboxylic acid With dmap In dichloromethane for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 8h; | 80.3% |
Stage #1: 1-hexadecylcarboxylic acid With 1,1'-carbonyldiimidazole In chloroform-d1 at 20℃; for 0.75h; Condensation; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform-d1 at 20℃; for 24h; Acylation; |
2-chloroethyl phosphorodichloridate
1,2-dipalmitoyl-sn-glycerol
trimethylamine
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Stage #1: 2-chloroethyl phosphorodichloridate; 1,2-dipalmitoyl-sn-glycerol With triethylamine In dichloromethane phosphorylation; Stage #2: With water; triethylamine In dichloromethane Hydrolysis; Stage #3: trimethylamine In ethanol at 70 - 80℃; for 72h; Substitution; | 60.5% |
2-(1',2'-dipalmitoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane
trimethylamine
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 16h; Ring cleavage; addition; | 56% |
palmitic anhydride
1-palmitoyl-sn-glycero-3-phosphocholine
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With dmap In chloroform for 42h; Ambient temperature; | 0.21 g |
choline tosylate
triethylammonium 1,2-di-O-hexadecanoyl-sn-glycerol 3-hydrogenphosphonate
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; water; iodine 2.) 5 min; Yield given. Multistep reaction; |
Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-phosphoryloxy]-ethyl}-trimethyl-ammonium;
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With trimethylamine In toluene for 10h; Ambient temperature; Yield given; |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In chloroform Ambient temperature; Yield given; |
2-(N,N-dimethylamino)ethanol
1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid
methyl iodide
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; sodium tetraphenyl borate Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With chloroform |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With ethanol; platinum Hydrogenation; |
Conditions | Yield |
---|---|
With toluene Behandeln einer Loesung des Reaktionsprodukts in Methanol mit Silbercarbonat; |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With ethanol; platinum Hydrogenation; |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With ethanol; platinum Hydrogenation; |
palmitic acid carboimidazolide
L-glycero-3-phosphorylcholine
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 24h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: DBU / 24 h View Scheme |
1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 69.5 percent / BCl3 / CH2Cl2 / 20 °C 2.1: Et3N / CH2Cl2 2.2: H2O; Et3N / CH2Cl2 2.3: 60.5 percent / ethanol / 72 h / 70 - 80 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 69.5 percent / DMAP; DCC / CH2Cl2 / 24 h / 20 °C 2.1: 69.5 percent / BCl3 / CH2Cl2 / 20 °C 3.1: Et3N / CH2Cl2 3.2: H2O; Et3N / CH2Cl2 3.3: 60.5 percent / ethanol / 72 h / 70 - 80 °C View Scheme |
1,2-dipalmitoyl-sn-glycerol
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / Et3N / benzene / 16 h / 20 °C 2: 56 percent / Et3N / acetonitrile / 16 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: POCl3, Et3N / CHCl3 / Ambient temperature 2: pyridine / CHCl3 / Ambient temperature 3: 10percent aq. NaHCO3 / CHCl3 / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: Et3N / CHCl3 / 0.08 h / Ambient temperature 2: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 3: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 4: Me3N / toluene / 10 h / Ambient temperature View Scheme |
1,2-dipalmitoyl-3-triphenylmethyl-sn-glycerol
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 74 percent / 12N HCl / CHCl3; methanol / 18 h / 0 °C 2: 90 percent / Et3N / benzene / 16 h / 20 °C 3: 56 percent / Et3N / acetonitrile / 16 h / 20 °C View Scheme |
(R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitate
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CHCl3 / Ambient temperature 2: 10percent aq. NaHCO3 / CHCl3 / Ambient temperature View Scheme |
Hexadecanoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 2: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 3: Me3N / toluene / 10 h / Ambient temperature View Scheme |
choline tosylate
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 2: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 3: Me3N / toluene / 10 h / Ambient temperature View Scheme |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 2: Me3N / toluene / 10 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KOAc / various solvent(s) / 42 h / Heating 2: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 94 percent / NEt4I / 0.42 h / Heating 2: KOAc / various solvent(s) / 42 h / Heating 3: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / diethyl ether / -15 °C 2: KOAc / various solvent(s) / 42 h / Heating 3: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme |
L-dipalmitoylphosphatidylcholine
1-palmitoyl-sn-glycero-3-phosphocholine
Conditions | Yield |
---|---|
With sodium docusate; phospholipase A2 In aq. buffer at 40℃; for 0.5h; pH=8.5; | 99% |
With Tris-HCl buffer; calcium chloride; phospholipase A2 In diethyl ether; ethanol at 20℃; for 7h; pH=8.0; deacylation; | 77% |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With water In ethanol at 25℃; Enzymatic reaction; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With calcium chloride In dichloromethane; tris hydrochloride at 35℃; for 16h; pH=8; Inert atmosphere; Darkness; | 89% |
L-homoserine
L-dipalmitoylphosphatidylcholine
A
choline
B
Hexadecanoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester
Conditions | Yield |
---|---|
With acetate buffer; phospholipase D In chloroform; water at 45℃; for 2h; | A n/a B 83% |
Conditions | Yield |
---|---|
With sodium chloride In diethyl ether; water at 30℃; for 24h; phospholipase D from Actinomadura sp. strain No. 362; | 76% |
L-dipalmitoylphosphatidylcholine
uridine
Hexadecanoic acid (R)-2-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester
Conditions | Yield |
---|---|
With acetate buffer; calcium chloride; phospholipase D-P In chloroform; water at 45℃; for 6h; pH 6.0; | 75% |
With acetate buffer; phospholipase D-P In chloroform; water at 25℃; for 0.166667h; Rate constant; pH 6.0; Linewaever-Burk plots; further nucleosides; |
Conditions | Yield |
---|---|
With D-glucose In chloroform; acetate buffer at 37℃; for 2h; pH=6.0; | 54.3% |
L-dipalmitoylphosphatidylcholine
1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)cytosine
Conditions | Yield |
---|---|
In chloroform; water at 40℃; phospholipase D from Streptomyces sp. AA 586; | 42% |
6-hydroxyhexyl β-lactoside
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With Streptomyces sp. phospholipase D (EC 3.1.4.4); calcium chloride In phosphate buffer; chloroform at 30℃; for 80h; pH=5.5; | 36% |
L-dipalmitoylphosphatidylcholine
Conditions | Yield |
---|---|
With Streptomyces sp. phospholipase D (EC 3.1.4.4); calcium chloride In phosphate buffer; chloroform at 30℃; pH=5.5; | 33% |
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; | 30% |
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; |
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phopholipase-D; |
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; |
ethanol
L-dipalmitoylphosphatidylcholine
(R)-1-(ethoxy-hydroxy-phosphoryloxy)-2,3-bis-palmitoyloxy-propane; sodium-salt
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; |
d(4)-methanol
L-dipalmitoylphosphatidylcholine
C36H67(2)H3O8P(1-)*Na(1+)
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; |
L-dipalmitoylphosphatidylcholine
neplanocin A
C46H79N5O10P(1-)*Na(1+)
Conditions | Yield |
---|---|
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction; |
L-dipalmitoylphosphatidylcholine
Mizoribine<*>
C44H78N3O13P(2-)*H(1+)*Na(1+)
Conditions | Yield |
---|---|
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction; |
L-dipalmitoylphosphatidylcholine
butan-1,1,2,2,3,3,4,4,4-d9-1-ol-d
C39H67(2)H9O8P(1-)*Na(1+)
Conditions | Yield |
---|---|
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D; |
L-dipalmitoylphosphatidylcholine
5-fluorouridine
C44H77FN2O13P(1-)*Na(1+)
Conditions | Yield |
---|---|
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 5.6, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction; |
L-dipalmitoylphosphatidylcholine
5-fluorocytidine
C44H78FN3O12P(1-)*Na(1+)
Conditions | Yield |
---|---|
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 5.6, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction; |
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