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990-91-0

Basic Information
CAS No.: 990-91-0
Name: Diphosphoric acid,P,P,P',P'-tetrakis(phenylmethyl) ester
Molecular Structure:
Molecular Structure of 990-91-0 (Diphosphoric acid,P,P,P',P'-tetrakis(phenylmethyl) ester)
Formula: C28H28O7P2
Molecular Weight: 538.46
Synonyms: Benzylpyrophosphate ([(C7H7O)2PO]2O) (7CI);Diphosphoric acid, tetrakis(phenylmethyl)ester (9CI);Pyrophosphoric acid, tetrabenzyl ester (8CI);Tetrabenzyldiphosphate;Tetrabenzyl pyrophosphate;Tetrabenzylpyrophosphate;
EINECS: 628-817-3
Density: 1.289 g/cm3
Melting Point: 63-66 °C(lit.)
Boiling Point: 601.6 °C at 760 mmHg
Flash Point: 330.4 °C
Solubility: Slightly soluble in water.
Appearance:
Hazard Symbols: CorrosiveC
Risk Codes: 34
Safety: 26-36/37/39-45
Transport Information: UN 3261 8/PG 2
PSA: 99.91000
LogP: 8.08640
Synthetic route
1623-08-1

phosphoric acid dibenzyl ester

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
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%
17176-77-1

Dibenzyl phosphite

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
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;
18826-95-4, 107-88-0

1.3-butanediol

15205-57-9

tribenzyl phosphite

A

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

B

538-60-3

dibenzyl hydrogen phosphite

C

123417-01-6

3-(dibenzyl)phosphoryloxy-1-methyl-1-propanol

Conditions
ConditionsYield
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%
110-86-1

pyridine

1623-08-1

phosphoric acid dibenzyl ester

98-59-9

p-toluenesulfonyl chloride

71-43-2

benzene

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

110-86-1

pyridine

1623-08-1

phosphoric acid dibenzyl ester

98-74-8

4-Nitrobenzenesulfonyl chloride

71-43-2

benzene

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

56-23-5

tetrachloromethane

17176-77-1

Dibenzyl phosphite

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
With potassium hydroxide
75-62-7

Bromotrichloromethane

17176-77-1

Dibenzyl phosphite

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
With potassium hydroxide
538-37-4

dibenzyl phosphochloridate

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
With potassium hydroxide
1623-08-1

phosphoric acid dibenzyl ester

121-44-8

triethylamine

75-05-8

acetonitrile

407-25-0

trifluoroacetic anhydride

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

56-23-5

tetrachloromethane

17176-77-1

Dibenzyl phosphite

aqueous KOH

aqueous KOH

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

75-62-7

Bromotrichloromethane

17176-77-1

Dibenzyl phosphite

aqueous KOH

aqueous KOH

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

538-37-4

dibenzyl phosphochloridate

aqueous KOH

aqueous KOH

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

91-66-7

N,N-diethylaniline

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
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
100-51-6

benzyl alcohol

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
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
100-51-6

benzyl alcohol

sodium

sodium

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H3PO4, Et3N, trichloroacetonitrile
2: DCC
View Scheme
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

134098-64-9

1-O-(tert-butyldimethylsilyl)-3-(2-hydroxy-4,6-dimethylphenyl)-3,3-dimethylpropan-1-ol

153910-63-5

dibenzyl (2-(4-((tert-butyldimethylsilyl)oxy)-2-methylbutan-2-yl)-3,5-dimethylphenyl) phosphate

Conditions
ConditionsYield
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
1032939-16-4

1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-α-D-xylopyranoside

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1032939-17-5

1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-α-D-xylopyranoside-4-O-dibenzylphosphate

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

550346-02-6

benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

1032939-14-2

1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-β-L-arabinopyranoside-4-O-dibenzylphosphate

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

81429-51-8

Glycerinaldehyd-diethylacetal-3-triphenylmethylether

1032939-18-6

2-dibenzylphosphoryl-3-triphenylmethylglyceraldehyde diethyl acetal

Conditions
ConditionsYield
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%
methanol-CH2Cl2

methanol-CH2Cl2

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

123-08-0

4-hydroxy-benzaldehyde

156745-33-4

dibenzyl (4-formylphenyl) phosphate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran98%

2-acetamido-3-O-acetyl-2-deoxy-4,6-O-(di-tert-butylsilandiyl)-D-glucopyranose

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1092110-69-4

C32H46NO10PSi

Conditions
ConditionsYield
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%
10210-17-0

3-(4-hydroxyphenyl)propan-1-ol

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

3-[4-(dibenzyl)phosphoryloxy]phenyl-1-propanol

Conditions
ConditionsYield
With tetrahexylammonium iodide; silver(l) oxide In dichloromethane at 20℃; for 20h;97%
3360-41-6

4-phenyl-butan-1-ol

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

136025-58-6

4-phenylbutyl-dibenzylphosphate

Conditions
ConditionsYield
With titanium(IV) tetrabutoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;97%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1346041-88-0

(1,1-bis-(hydroxymethyl)propyl)carbamic acid benzyl ester

2-(benzyloxycarbonyl)amino-2-ethyl-3-hydroxylpropyl dibenzyl phosphate

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

156745-33-4

dibenzyl (4-formylphenyl) phosphate

Conditions
ConditionsYield
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%
1032939-22-2

1-O-benzyl-2,3-isopropylidene-β-L-ribopyranose

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1032939-23-3

1-O-benzyl-2,3-isopropylidene-β-L-ribopyranoside-4-O-dibenzylphosphate

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

(S)-1-(3,4,5-trimethoxyphenyl)-4-(3-hydroxy-4-methoxyphenyl)-3-methyleneazetidine-2-one

C34H34NO9P

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 0 - 20℃; for 0.25h; Schlenk technique;96%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

129365-65-7

(1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-(1-ethoxy-ethoxy)-6-fluoro-cyclohexane-1,2,4-triol

129365-66-8

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
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 8h;95%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

90357-98-5

dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane; ethylbenzene at -78℃; for 3h;95%
691409-52-6

N6-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine

990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

691409-55-9

N6-methyl-2-(2-phenylethynyl)-2'-deoxyadenosine-3',5'-bis(dibenzylphosphate)

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1256037-41-8

2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one

1256037-56-5

2-(3-fluorophenyl)-6-methoxyquinoline-4,5-diyl bis(dibenzylphosphate)

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α/β-D-glucopyranose

1334530-12-9

(2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-α-D-glucopyranosyl)-1-dibenzylphosphate

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

1256037-41-8

2-(3-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one

1256037-56-5

2-(3-fluorophenyl)-6-methoxyquinoline-4,5-diyl bis(dibenzylphosphate)

Conditions
ConditionsYield
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%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

207564-31-6

1,5-anhydro-3,4-di-O-benzyl-2-deoxy-5a-carba-D-arabino-hex-1-enitol

C35H37O6P

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;95%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

262863-48-9

2-chloro-9-[(diethanolamino)carboxymethyl]-6-methylamino-purine

262863-49-0

9-bis(2-dibenzylphosphatoethylamino)-acetyl-2-chloro-6-methylamino-purine

Conditions
ConditionsYield
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%
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    Diphosphoric acid,P,P,P',P'-tetrakis(phenylmethyl) ester 990-91-0

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    Phosphorylating reagent, Tetrabenzyl pyrophosphate CAS:990-91-0

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  • dibenzyl {[bis(benzyloxy)phosphoryl]oxy}phosphonate

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Specification

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