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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

362883-5G:
362883-BULK:
362883-VAR:
362883-1G:

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 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)
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
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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