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362883

Sigma-Aldrich

Dibenzyl N,N-diethylphosphoramidite

technical grade, 85%

Synonym(s):

TTC

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About This Item

Linear Formula:
(C2H5)2NP(OCH2C6H5)2
CAS Number:
67746-43-4
Molecular Weight:
317.36
Beilstein:
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

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

93.2 °F - closed cup

Flash Point(C)

34 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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 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)
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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