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418633

Sigma-Aldrich

Tetrabenzyl pyrophosphate

98%

Synonym(s):

Pyrophosphoric acid tetrabenzyl ester, Tetrabenzyl diphosphate

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About This Item

Linear Formula:
(C6H5CH2O)2P(O)OP(O)(OCH2C6H5)2
CAS Number:
990-91-0
Molecular Weight:
538.47
Beilstein:
2068292
MDL number:
MFCD00051941
UNSPSC Code:
12352100
PubChem Substance ID:
24866232
NACRES:
NA.22

Assay

98%

mp

63-66 °C (lit.)

functional group

phenyl
phosphate

storage temp.

−20°C

SMILES string

O=P(OCc1ccccc1)(OCc2ccccc2)OP(=O)(OCc3ccccc3)OCc4ccccc4

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

InChI key

NSBNXCZCLRBQTA-UHFFFAOYSA-N

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Application

Tetrabenzyl pyrophosphate may be employed for the following studies:
  • Fabrication of Pb2+-selective membrane electrodes.
  • Preparation of synthetic nucleotides, phosphates of the 3,6-dideoxyhexoses.
  • As phosphorylating reagent for the synthesis of Und-PP-Bac (undecaprenyl pyrophosphate = Und-PP; Bac = unusual sugar bacillosamine).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000226897
0000203676
BGBC3223V
BGBC2860V
BCBF9560V

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The Journal of Organic Chemistry, 59, 2279-2279 (1994)
N S Utkina et al.
Bioorganicheskaia khimiia, 15(10), 1375-1383 (1989-10-01)
Interaction of lithium alcoholates of 2,4-di-O-benzoates of paratose and abequose with tetrabenzyl pyrophosphate gave alpha-phosphates of the 3,6-dideoxyhexoses, further converted into the corresponding cytidine-5'-diphosphate derivatives. These synthetic nucleotides were shown to participate in the biosynthesis of the O-specific polysaccharides for
Eranthie Weerapana et al.
Journal of the American Chemical Society, 127(40), 13766-13767 (2005-10-06)
The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can
D Xu et al.
Talanta, 51(2), 365-371 (2008-10-31)
Tetrabenzyl pyrophosphate and diphenylphosphinic anhydride, with two phosphoryl groups (PO) as ligating sites, can be used as novel ionophores to make Pb(2+)-selective membrane electrodes. A good result was obtained with tetrabenzyl pyrophosphate, and the electrode based on this ionophore and
Solvolysis of Tetrabenzyl Pyrophosphate. Catalysis by Imidazole1
Blakeley R, et al.
Journal of the American Chemical Society, 88(1), 112-119 (1966)
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