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362883

Dibenzyl N,N-diethylphosphoramidite

Name: Dibenzyl <I>N</I>,<I>N</I>-diethylphosphoramidite
Brand: ALDRICH

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

Assay:

85%

Form:

liquid

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Properties

grade

technical grade

Quality Level

100

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

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

Description

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

GHS02,GHS07

signalword

Warning

hcodes

H226,H315,H319,H335

pcodes

P210 - P302 + P352 - P305 + P351 + P338

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

Regulatory Information

危险化学品

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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)

Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

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

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Global Trade Item Number

SKU	GTIN
362883-1G	04061837656774
362883-5G	04061837656781