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439606

Sigma-Aldrich

Diallyl N,N-diisopropylphosphoramidite

Sinónimos:

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

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About This Item

Fórmula lineal:
[(CH3)2CH]2NP(OCH2CH=CH2)2
Número de CAS:
126429-21-8
Peso molecular:
245.30
Beilstein/REAXYS Number:
4383514
MDL number:
MFCD00216647
UNSPSC Code:
12352100
PubChem Substance ID:
24867522
NACRES:
NA.22

form

liquid

refractive index

n20/D 1.456 (lit.)

bp

130 °C (lit.)

density

0.928 g/mL at 25 °C (lit.)

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

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_germany

WGK 3

flash_point_f

89.6 °F - closed cup

flash_point_c

32 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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)
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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