phosphoric acid dibenzyl ester
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In Isopropyl acetate at 0 - 6℃; for 1.5h; Inert atmosphere; | 96% |
With N,N-dicyclohexylurea In toluene at 20℃; for 5h; | 95% |
With dicyclohexyl-carbodiimide In Isopropyl acetate at 3℃; for 0.916667 - 1.08333h; | 91% |
Dibenzyl phosphite
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; copper(ll) bromide In tetrahydrofuran at 25℃; for 15h; | 90% |
With tetrachloromethane; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In toluene at 60℃; for 0.5h; | 88% |
With N-chloro-succinimide; benzene anschliessendes Behandeln mit Phosphorsaeure-dibenzylester und Triaethylamin; |
1.3-butanediol
tribenzyl phosphite
A
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
B
dibenzyl hydrogen phosphite
C
3-(dibenzyl)phosphoryloxy-1-methyl-1-propanol
Conditions | Yield |
---|---|
Stage #1: tribenzyl phosphite With iodine In dichloromethane at 0 - 20℃; for 0.416667h; Stage #2: 1.3-butanediol With pyridine In dichloromethane at 20℃; for 0.5h; | A n/a B n/a C 65% |
pyridine
phosphoric acid dibenzyl ester
p-toluenesulfonyl chloride
benzene
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
pyridine
phosphoric acid dibenzyl ester
4-Nitrobenzenesulfonyl chloride
benzene
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
tetrachloromethane
Dibenzyl phosphite
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With potassium hydroxide |
Bromotrichloromethane
Dibenzyl phosphite
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide |
phosphoric acid dibenzyl ester
triethylamine
acetonitrile
trifluoroacetic anhydride
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
tetrachloromethane
Dibenzyl phosphite
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Bromotrichloromethane
Dibenzyl phosphite
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene; PCl3 / 5 °C / anschliessendes Behandeln mit Wasser 2: aqueous KOH View Scheme | |
Multi-step reaction with 2 steps 1: benzene; PCl3 / 5 °C / anschliessendes Behandeln mit Wasser 2: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene; PCl3 / 5 °C / anschliessendes Behandeln mit Wasser 2: aqueous KOH View Scheme | |
Multi-step reaction with 2 steps 1: benzene; PCl3 / 5 °C / anschliessendes Behandeln mit Wasser 2: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H3PO4, Et3N, trichloroacetonitrile 2: DCC View Scheme |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
1-O-(tert-butyldimethylsilyl)-3-(2-hydroxy-4,6-dimethylphenyl)-3,3-dimethylpropan-1-ol
dibenzyl (2-(4-((tert-butyldimethylsilyl)oxy)-2-methylbutan-2-yl)-3,5-dimethylphenyl) phosphate
Conditions | Yield |
---|---|
Stage #1: 1-O-(tert-butyldimethylsilyl)-3-(2-hydroxy-4,6-dimethylphenyl)-3,3-dimethylpropan-1-ol With potassium tert-butylate In tetrahydrofuran at 60℃; for 0.0833333h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 60℃; for 1h; | 100% |
With potassium tert-butylate In tetrahydrofuran at 60℃; for 0.75h; | 87% |
Stage #1: 1-O-(tert-butyldimethylsilyl)-3-(2-hydroxy-4,6-dimethylphenyl)-3,3-dimethylpropan-1-ol With potassium tert-butylate In tetrahydrofuran at 60℃; for 0.0833333h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran for 1h; Reflux; | 87.2% |
With potassium tert-butylate In tetrahydrofuran at 60℃; | 43.8% |
In N,N-dimethyl-formamide; mineral oil |
1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-α-D-xylopyranoside
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-α-D-xylopyranoside-4-O-dibenzylphosphate
Conditions | Yield |
---|---|
Stage #1: 1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-α-D-xylopyranoside With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -40 - 20℃; for 3.33333h; | 100% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside
1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-β-L-arabinopyranoside-4-O-dibenzylphosphate
Conditions | Yield |
---|---|
Stage #1: benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -40 - 20℃; for 3.33333h; | 100% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Glycerinaldehyd-diethylacetal-3-triphenylmethylether
2-dibenzylphosphoryl-3-triphenylmethylglyceraldehyde diethyl acetal
Conditions | Yield |
---|---|
Stage #1: Glycerinaldehyd-diethylacetal-3-triphenylmethylether With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -40 - 20℃; | 99% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
4-hydroxy-benzaldehyde
dibenzyl (4-formylphenyl) phosphate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran | 98% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
C32H46NO10PSi
Conditions | Yield |
---|---|
Stage #1: 2-acetamido-3-O-acetyl-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-D-glucopyranose With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -78 - 20℃; stereoselective reaction; | 98% |
3-(4-hydroxyphenyl)propan-1-ol
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With tetrahexylammonium iodide; silver(l) oxide In dichloromethane at 20℃; for 20h; | 97% |
4-phenyl-butan-1-ol
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
4-phenylbutyl-dibenzylphosphate
Conditions | Yield |
---|---|
With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; | 97% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
(1,1-bis-(hydroxymethyl)propyl)carbamic acid benzyl ester
Conditions | Yield |
---|---|
With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 16h; Time; Inert atmosphere; chemoselective reaction; | 97% |
With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Solvent; Inert atmosphere; | 96% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
dibenzyl (4-formylphenyl) phosphate
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-benzaldehyde With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 70℃; for 1.16667h; | 96% |
1-O-benzyl-2,3-isopropylidene-β-L-ribopyranose
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
1-O-benzyl-2,3-isopropylidene-β-L-ribopyranoside-4-O-dibenzylphosphate
Conditions | Yield |
---|---|
Stage #1: 1-O-benzyl-2,3-isopropylidene-β-L-ribopyranose With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -40 - 20℃; for 5.66667h; | 96% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane at 0 - 20℃; for 0.25h; Schlenk technique; | 96% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
(1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-(1-ethoxy-ethoxy)-6-fluoro-cyclohexane-1,2,4-triol
Phosphoric acid dibenzyl ester (1S,2S,3R,4S,5S,6S)-2-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 8h; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
2,3,4,6-tetra-O-benzyl-D-mannopyranose
dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane; ethylbenzene at -78℃; for 3h; | 95% |
N6-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
N6-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine-3',5'-bis(dibenzylphosphate)
Conditions | Yield |
---|---|
Stage #1: N6-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine With potassium tert-butylate In tetrahydrofuran at -40℃; for 0.0833333h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at -40℃; for 0.5h; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one
2-(3-fluorophenyl)-6-methoxyquinoline-4,5-diyl bis(dibenzylphosphate)
Conditions | Yield |
---|---|
Stage #1: 2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one With sodium hydride In tetrahydrofuran at 0℃; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran for 0.416667h; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
(2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate
Conditions | Yield |
---|---|
Stage #1: 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α/β-D-glucopyranose With ethylbenzene; lithium diisopropyl amide In tetrahydrofuran; n-heptane at -78℃; for 0.25h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran; n-heptane at -78 - 0℃; for 3h; Inert atmosphere; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one
2-(3-fluorophenyl)-6-methoxyquinoline-4,5-diyl bis(dibenzylphosphate)
Conditions | Yield |
---|---|
Stage #1: 2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one With sodium hydride In tetrahydrofuran at -1 - 1℃; for 1h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran for 0.416667h; Product distribution / selectivity; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
1,5-anhydro-3,4-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 95% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
2-chloro-9-[(diethanolamino)carboxymethyl]-6-methylamino-purine
9-bis(2-dibenzylphosphatoethylamino)-acetyl-2-chloro-6-methylamino-purine
Conditions | Yield |
---|---|
Stage #1: 2-chloro-9-[(diethanolamino)carboxymethyl]-6-methylamino-purine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h; deprotonation; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 0 - 25℃; for 12h; phosphorylation; Further stages.; | 94% |
The CAS register number of Tetrabenzyl pyrophosphate is 990-91-0. It also can be called as Pyrophosphoric acid tetrabenzyl ester and the IUPAC name about this chemical is dibenzyl bis(phenylmethoxy)phosphoryl phosphate. It belongs to the following product categories, such as Biochemistry, Nucleosides, Nucleotides & Related Reagents, Phosphorylating and Phosphorothioating Agents, Phosphorylation, Protecting Agents, Phosphorylating Agents & Condensing Agents, Synthetic Organic Chemistry and so on.
Physical properties about Tetrabenzyl pyrophosphate are: (1)ACD/LogP: 6.01; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 6.01; (4)ACD/LogD (pH 7.4): 6.01; (5)ACD/BCF (pH 5.5): 21756.89; (6)ACD/BCF (pH 7.4): 21756.89; (7)ACD/KOC (pH 5.5): 44303.46; (8)ACD/KOC (pH 7.4): 44303.46; (9)#H bond acceptors: 7; (10)#Freely Rotating Bonds: 14; (11)Polar Surface Area: 99.91Å2; (12)Index of Refraction: 1.59; (13)Molar Refractivity: 141 cm3; (14)Molar Volume: 417.4 cm3; (15)Polarizability: 55.89x10-24cm3; (16)Surface Tension: 52.2 dyne/cm; (17)Enthalpy of Vaporization: 86.23 kJ/mol; (18)Boiling Point: 601.6 °C at 760 mmHg; (19)Vapour Pressure: 8.62E-14 mmHg at 25°C.
Uses of Tetrabenzyl pyrophosphate: it can be used to produce dibenzyl phosphorofluoridate at Ambient temperature. This reaction will need reagent CsF and solvent acetonitrile. The yield is about 80%.
When you are using this chemical, please be cautious about it as the following:
This chemical can causes burns. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice and in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OCc1ccccc1)(OCc2ccccc2)OP(=O)(OCc3ccccc3)OCc4ccccc4
(2)InChI: InChI=1/C28H28O7P2/c29-36(31-21-25-13-5-1-6-14-25,32-22-26-15-7-2-8-16-26)35-37(30,33-23-27-17-9-3-10-18-27)34-24-28-19-11-4-12-20-28/h1-20H,21-24H2
(3)InChIKey: NSBNXCZCLRBQTA-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C28H28O7P2/c29-36(31-21-25-13-5-1-6-14-25,32-22-26-15-7-2-8-16-26)35-37(30,33-23-27-17-9-3-10-18-27)34-24-28-19-11-4-12-20-28/h1-20H,21-24H2
(5)Std. InChIKey: NSBNXCZCLRBQTA-UHFFFAOYSA-N
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