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Merck

362883

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24862337
MDL number:
MFCD00191987
Beilstein/REAXYS Number:
4189915

Key Documents

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Product Name

Dibenzyl N,N-diethylphosphoramidite, technical grade, 85%

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

SMILES string

CCN(CC)P(OCc1ccccc1)OCc2ccccc2

InChI key

NLGUJOVLAXLSMX-UHFFFAOYSA-N

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.)

functional group

amine
phenyl

storage temp.

2-8°C

Quality Level

100

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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

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.

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000220241
0000220241
MKCM1152
MKBF3556V
MKBF3556

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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)
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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