439606

Diallyl-N,N-diisopropylphosphoramidit

• Synonym(e): N,N-Bis(1-methylethyl)phosphoramidous acid di-2-propenyl ester, Diallyloxy(diisopropylamino)phosphine
• Lineare Formel: [(CH₃)₂CH]₂NP(OCH₂CH=CH₂)₂
• CAS-Nummer: 126429-21-8
• Molekulargewicht: 245.30
• Beilstein: 4383514
• MDL-Nummer: MFCD00216647
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24867522
• NACRES: NA.22

Eigenschaften

• Form: liquid
• Qualitätsniveau: 200
• Brechungsindex: n20/D 1.456 (lit.)
• bp: 130 °C (lit.)
• Dichte: 0.928 g/mL at 25 °C (lit.)
• Lagertemp.: 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
• InChIKey: QBLCHHSGJTUNSJ-UHFFFAOYSA-N

Beschreibung

Anwendung

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

Sicherheitshinweise

• Piktogramme: GHS02,GHS07
• Signalwort: Warning
• H-Sätze: H226,H315,H319,H335
• P-Sätze: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 89.6 °F - closed cup
• Flammpunkt (°C): 32 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter