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362883

Sigma-Aldrich

Dibenzyl N,N-diethylphosphoramidite

technical grade, 85%

Sinónimos:

TTC

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About This Item

Fórmula lineal:
(C2H5)2NP(OCH2C6H5)2
Número de CAS:
67746-43-4
Peso molecular:
317.36
Beilstein/REAXYS Number:
4189915
MDL number:
MFCD00191987
UNSPSC Code:
12352100
PubChem Substance ID:
24862337
NACRES:
NA.22

grade

technical grade

vapor pressure

0.71 psi ( 55 °C)

assay

85%

form

liquid

refractive index

n20/D 1.545 (lit.)

density

1.06 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCN(CC)P(OCc1ccccc1)OCc2ccccc2

InChI

1S/C18H24NO2P/c1-3-19(4-2)22(20-15-17-11-7-5-8-12-17)21-16-18-13-9-6-10-14-18/h5-14H,3-4,15-16H2,1-2H3

InChI key

NLGUJOVLAXLSMX-UHFFFAOYSA-N

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General description

Dibenzyl N,N-diethylphosphoramidite is repoted to be suitable reagent for the efficient 1H-tetrazole-catalyzed ′phosphite-triester′ phosphorylation of the protected serine derivatives.

Application

Dibenzyl N,N-diethylphosphoramidite may be used:
  • as phosphitylating reagent in the synthesis of glycosyl phosphites and phosphates
  • for phosphorylating the alcohols
  • in the preparation of 6-dibenzylphosphate-1,3,5-tri-O-PMB-myo-inositol

For use with

Referencia del producto
Descripción
Precios

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

93.2 °F - closed cup

flash_point_c

34 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Synthesis of Casein-Related Peptides and Phosphopeptides. V. The Efficient Global'Phosphite-Triester'Phosphorylation of Protected Serine Derivatives and Peptides by Using Dibenzyl or Di-t-butyl N, N-Diethylphosphoramidite.
Perich JW and Johns RB.
Australian Journal of Chemistry, 43(10), 1623-1632 (1990)
Peter A Jordan et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(48), 20620-20624 (2010-05-05)
Despite the ubiquitous use of phosphoramidite chemistry in the synthesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for phosphate ester synthesis. We have discovered that a tetrazole-functionalized peptide, in the presence of 10-Å molecular sieves, functions as an
Synthesis of dibenzyl glycosyl phosphites using dibenzyl N, N-diethylphosphoramidite as phosphitylating reagent: an effective route to glycosyl phosphates, nucleotides, and glycosides.
Sim MM, et al.
Journal of the American Chemical Society, 115(6), 2260-2267 (1993)
Qiao Liao et al.
Acta pharmacologica Sinica, 40(10), 1314-1321 (2019-05-08)
Irisin, a myokine, is cleaved from the extracellular portion of fibronectin domain-containing 5 protein in skeletal muscle and myocardium and secreted into circulation as a hormone during exercise. Irisin has been found to exert protective effects against lung and heart injuries.

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