Tetrabenzyl pyrophosphate

Name: Tetrabenzyl pyrophosphate
Brand: ALDRICH
Price: 355 USD

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/REAXYS Number:

2068292

MDL number:

MFCD00051941

UNSPSC Code:

12352100

PubChem Substance ID:

24866232

NACRES:

NA.22

Key Documents

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Quality Level

200

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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Show Differences

1 of 4

This Item	93397	165956	8.21197
Sigma-Aldrich 418633 Tetrabenzyl pyrophosphate	Sigma-Aldrich 93397 Tris(tetrabutylammonium) hydrogen pyrophosphate	Sigma-Aldrich 165956 Methyl benzenesulfonate	Sigma-Aldrich 8.21197 Triphenyl phosphate
assay 98%	assay ≥97.0% (calc. on dry substance, T)	assay 98%	assay ≥99.0% (GC)
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 200
mp 63-66 °C (lit.)	mp -	mp -	mp 48-50 °C
storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-30°C
functional group phenyl	functional group amine, phosphate	functional group sulfonic acid	functional group -

Application

Tetrabenzyl pyrophosphate may be employed for the following studies:

Fabrication of Pb²⁺-selective membrane electrodes.[1]
Preparation of synthetic nucleotides, phosphates of the 3,6-dideoxyhexoses.[2]
As phosphorylating reagent for the synthesis of Und-PP-Bac (undecaprenyl pyrophosphate = Und-PP; Bac = unusual sugar bacillosamine).[3]

pictograms

GHS05

signalword

Danger

hcodes

H314

pcodes

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Journal of the Chemical Society. Perkin Transactions 1, 729-729 (1992)

Solvolysis of Tetrabenzyl Pyrophosphate. Catalysis by Imidazole1

Blakeley R, et al.

Journal of the American Chemical Society, 88(1), 112-119 (1966)

The Journal of Organic Chemistry, 59, 2279-2279 (1994)

Investigating bacterial N-linked glycosylation: synthesis and glycosyl acceptor activity of the undecaprenyl pyrophosphate-linked bacillosamine.

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

[Synthesis of cytidine diphosphate-3,6-dideoxyhexoses--donors of glycosyl residues in the biosynthesis of O-specific polysaccharides of Salmonella of serogroups A, B and C].

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

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Tetrabenzyl pyrophosphate