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439606

Sigma-Aldrich

Diallyl N,N-diisopropylphosphoramidite

Synonym(s):

N,N-Bis(1-methylethyl)phosphoramidous acid di-2-propenyl ester, Diallyloxy(diisopropylamino)phosphine

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About This Item

Linear Formula:
[(CH3)2CH]2NP(OCH2CH=CH2)2
CAS Number:
126429-21-8
Molecular Weight:
245.30
Beilstein:
4383514
MDL number:
MFCD00216647
UNSPSC Code:
12352100
PubChem Substance ID:
24867522
NACRES:
NA.22

form

liquid

Quality Level

200

refractive index

n20/D 1.456 (lit.)

bp

130 °C (lit.)

density

0.928 g/mL at 25 °C (lit.)

functional group

amine

storage temp.

2-8°C

SMILES string

CC(C)N(C(C)C)P(OCC=C)OCC=C

InChI

1S/C12H24NO2P/c1-7-9-14-16(15-10-8-2)13(11(3)4)12(5)6/h7-8,11-12H,1-2,9-10H2,3-6H3

InChI key

QBLCHHSGJTUNSJ-UHFFFAOYSA-N

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Application

Diallyl N,N-diisopropylphosphoramidite may be employed as phophorylating reagent in the following studies:
  • Preparation of peptide substrates.
  • Preparation of rhodamine dyes with phosphorylated CH2OH sites.
  • Synthesis of 3-[4-(bis-allyloxy-phosphoryloxy)-2(R)-hydroxy-3,3-dimethyl-butyrylamino]-thiopropionic acid-S-propylester.
Precursor involved in the synthesis of pharmacologically active molecules including:
  • Selective orally active S1P1 agonists
  • Water-soluble prodrugs of triazole CS-758 with antifungal activity
  • Fostriecin analogs as antitumor agents

Reactant involved in:
  • Phosphitylation of alcohols
  • Deallylation for the synthesis of nucleoside phosphoramidite
  • Posphitylation and stereoselective Pudovik rearrangement

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)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
04401PH
12925PQ
11330EN
11317DB
10328BN

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Solid-phase synthesis of adenosine phosphopeptides as potential bisubstrate inhibitors of protein kinases.
Medzihradszky D, et al.
Journal of the American Chemical Society, 116(21), 9413-9419 (1994)
Lutz Tautz et al.
European journal of organic chemistry, 2010(9), 1728-1735 (2010-03-01)
Co-translational myristoylation of the N-terminal glycine residue of diverse signaling proteins is required for membrane attachment and proper function of these molecules. The transfer of myristate from myristoyl-coenzyme A (myr-CoA) is catalyzed by the enzyme N-myristoyltransferase (Nmt). Nmt has been
Kirill Kolmakov et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(41), 12986-12998 (2012-09-13)
Fluorescent dyes emitting red light are frequently used in conventional and super-resolution microscopy of biological samples, although the variety of the useful dyes is limited. We describe the synthesis of rhodamine-based fluorescent dyes with absorption and emission maxima in the

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