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305995

Sigma-Aldrich

2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite

97%

Sinonimo/i:

Bis(diisopropylamino)(2-cyanoethoxy)phosphine

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About This Item

Formula condensata:
{[(CH3)2CH]2N}2POCH2CH2CN
Numero CAS:
102691-36-1
Peso molecolare:
301.41
Beilstein:
3590103
Numero MDL:
MFCD00012213
Codice UNSPSC:
12352100
ID PubChem:
24858468
NACRES:
NA.22

Saggio

97%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.470 (lit.)

P. eboll.

100 °C/0.5 mmHg (lit.)

Densità

0.949 g/mL at 25 °C (lit.)

Gruppo funzionale

amine

Temperatura di conservazione

−20°C

Stringa SMILE

CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C

InChI

1S/C15H32N3OP/c1-12(2)17(13(3)4)20(19-11-9-10-16)18(14(5)6)15(7)8/h12-15H,9,11H2,1-8H3
RKVHNYJPIXOHRW-UHFFFAOYSA-N

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Applicazioni

2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
  • in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotide
  • as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine
  • in situ preparation of deoxyribonucleoside phosphoramidites
  • in preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymine
  • as reagent for synthesizing phosphitylated nucleotides

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Pittogrammi

FlameExclamation mark
GHS02,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H226,H302,H317,H412

Classi di pericolo

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1B

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

119.3 °F - closed cup

Punto d’infiammabilità (°C)

48.5 °C - closed cup

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
MKCJ8691
MKCB0853V
MKBQ3495V
MKBB5710V
MKBB5710

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Vyacheslav V Filichev et al.
Bioorganic & medicinal chemistry, 12(11), 2843-2851 (2004-05-15)
Hexofuranosyl nucleosides are considered as conformationally restricted acyclic nucleosides using a furanose ring to link the diol backbone to the nucleobase. The phosphoramidite of 1-(2,3-dideoxy-beta-D-erythro-hexofuranosyl)thymine was synthesized from thymidine with formation of a new stereocentre at C-5' and the nucleoside
Lubomir V Nechev et al.
Chemical research in toxicology, 15(5), 607-613 (2002-05-23)
3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-6-hydroxy-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one is formed in low yield by the reaction of acrolein with 2'-deoxyguanosine. The nucleoside and an oligodeoxynucleotide containing it have been synthesized. For preparation of the nucleoside 2'-deoxyguanosine was alkylated at the N1 position using 1-bromo-3-butene to give 1-(3-butenyl)-2'-deoxyguanosine.
Arvind Misra et al.
Bioconjugate chemistry, 15(3), 638-646 (2004-05-20)
Synthesis of modified oligonucleotides in which the specific cytidine nucleoside analogues linked at 2'-OH position via a carbamate bond with an amino ethyl derivative of dansyl fluorophore is reported. For the multiple labeling of oligonucleotides, a strategy involving prelabeling at
Improved synthesis of (Pri2 N)2POCH2CH2CN.
J Nielsen et al.
Nucleic acids research, 15(8), 3626-3626 (1987-04-24)
Jonathan K Watts et al.
Nucleic acids research, 35(5), 1441-1451 (2007-02-08)
The synthesis of oligonucleotides containing 2'-deoxy-2'-fluoro-4'-thioarabinonucleotides is described. 2'-Deoxy-2'-fluoro-5-methyl-4'-thioarabinouridine (4'S-FMAU) was incorporated into 18-mer antisense oligonucleotides (AONs). 4'S-FMAU adopts a predominantly northern sugar conformation. Oligonucleotides containing 4'S-FMAU, unlike those containing FMAU, were unable to elicit E. coli or human RNase
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