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416436

Sigma-Aldrich

Dibenzyl N,N-diisopropylphosphoramidite

technical grade, 90%

Synonym(s):

Bis(benzyloxy)(diisopropylamino)phosphine, Dibenzyl N,N-diisopropylphosphoramidate, Dibenzyl diisopropylphosphoramidite, N,N-Diisopropyl dibenzyl phosphoramidate, [Bis(benzyloxy)phosphanyl]bis(propan-2-yl)amine

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About This Item

Linear Formula:
[(CH3)2CH]2NP(OCH2C6H5)2
CAS Number:
108549-23-1
Molecular Weight:
345.42
Beilstein:
3616864
MDL number:
MFCD00191988
UNSPSC Code:
12352100
PubChem Substance ID:
24866075
NACRES:
NA.22

grade

technical grade

Assay

90%

form

liquid

refractive index

n20/D 1.535 (lit.)

bp

130 °C/0.55 mmHg (lit.)

solubility

THF: soluble(lit.)
acetonitrile: soluble(lit.)
cold water: insoluble(lit.)
dichloromethane: soluble(lit.)

density

1.028 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)N(C(C)C)P(OCc1ccccc1)OCc2ccccc2

InChI

1S/C20H28NO2P/c1-17(2)21(18(3)4)24(22-15-19-11-7-5-8-12-19)23-16-20-13-9-6-10-14-20/h5-14,17-18H,15-16H2,1-4H3

InChI key

ANPWLBTUUNFQIO-UHFFFAOYSA-N

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Application

Dibenzyl N,N-diisopropylphosphoramidite may be used for the preparation of phosphopeptides. It may be used for the synthesis of a GDP (guanosine diphosphate) analog, SML-8-73-1.

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Pricing

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

156.2 °F - closed cup

Flash Point(C)

69 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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D M Andrews et al.
International journal of peptide and protein research, 38(5), 469-475 (1991-11-01)
A completely general method for the O-phosphorylation of peptides of any given composition using solid-phase methodology is described. Peptides were assembled using Fmoc amino acid active esters, with base used for Fmoc deprotection. Unprotected amino acid side chain hydroxyl groups
Jie Xue et al.
Organic letters, 6(9), 1365-1368 (2004-04-23)
[reaction: see text] A new one-step reaction has been developed for converting 4-azido-4-deoxy-d-galactoside into 4-deoxy-d-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite intermediate and a tetrazole-catalyzed elimination
Synthesis, 9, 1481-1485 (2004)
Sang Min Lim et al.
Angewandte Chemie (International ed. in English), 53(1), 199-204 (2013-11-22)
We report the synthesis of a GDP analogue, SML-8-73-1, and a prodrug derivative, SML-10-70-1, which are selective, direct-acting covalent inhibitors of the K-Ras G12C mutant relative to wild-type Ras. Biochemical and biophysical measurements suggest that modification of K-Ras with SML-8-73-1
D L Clemm et al.
Molecular endocrinology (Baltimore, Md.), 14(1), 52-65 (2000-01-11)
Human progesterone receptor (PR) is phosphorylated on multiple serine residues (at least seven sites) in a manner that involves distinct groups of sites coordinately regulated by hormone and different kinases. Progress on defining a functional role for PR phosphorylation has
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