102691-36-1

Basic information

• Product Name: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
• Synonyms: P-REAGENT;BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE;2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORAMIDITE;2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORDIAMIDITE;2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE;2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE;Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester;2-CYANOETHYL-N,N,N'',N''-TETRAISO-PROPYLPHOSPHORAMIDITE(P-REAGENT)
• CAS NO: 102691-36-1
• Molecular Formula: C₁₅H₃₂N₃OP
• Molecular Weight: 301.41
• EINECS: 2017-001-1
• Product Categories: Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Regant series;Nucleic acids;Phosphorylating and Phosphitylating Agents;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphoramidites;Phosphorus Compounds;OLED materials,pharm chemical,electronic
• Mol File: 102691-36-1.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 100 °C0.5 mm Hg(lit.)
• Flash Point: 141 °F
• Appearance: colorless/liquid
• Density: 0.949 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.470(lit.)
• Storage Temp.: 2-8°C
• PKA: 6.78±0.70(Predicted)
• Sensitive: moisture sensitive, store cold
• Stability: Explodes When Heated
• BRN: 3590103
• CAS DataBase Reference: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(102691-36-1)
• EPA Substance Registry System: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(102691-36-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 5-36/37/38-42/43-36/38
• Safety Statements: 3-26-36-24/25-23-45-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21-34
• HazardClass: 8
• PackingGroup: I
• Hazardous Substances Data: 102691-36-1(Hazardous Substances Data)

Usage

Description

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is a chemical compound that serves as a versatile reagent in the synthesis of phosphitylated nucleotides. It is a clear to cloudy colorless liquid and is widely utilized in various applications across different industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is used as a reagent for synthesizing phosphitylated nucleotides, which are essential building blocks in the development of new drugs and therapies.
Used in Nucleic Acid Synthesis:
In the field of molecular biology, this compound is used as a prosphoramidite reagent, which is crucial for the synthesis of 12-mer oligodeoxynucleotides. It acts as a phosphorylating agent in the synthesis of 1,2-diacyl-sn-glycerophosphatidylserine, a key component of cell membranes.
Used in Biochemistry Research:
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is employed in the in situ preparation of deoxyribonucleoside phosphoramidites, which are vital for the study of DNA and RNA structures and their interactions with other molecules.
Used in Organic Chemistry:
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is used in the 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. These complex organic molecules have potential applications in the development of novel therapeutic agents and diagnostic tools.

Upstream product

• 25152-20-9 5'-amino-5'-deoxythymidine 
• 76101-30-9 2-cyanoethyl phosphorodichloridite 
• 108-18-9 diisopropylamine 
• 109-78-4 3-Hydroxypropionitrile 
• 7719-12-2 phosphorus trichloride 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 

Downstream Products

• 330628-04-1 5'-O-(4,4'-dimethoxytrityl)-N-dimethyl-formamidine-2'-deoxyguanosine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite 
• 133339-60-3 2-<(N-benzyloxycarbonyl)amino>ethyl 2-cyanoethyl H-phosphonate 
• 139472-73-4 Benzoic acid 1-{2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-1-octadecanoylamino-ethyl}-hexadecyl ester 
• 154656-78-7 N⁶-dimethylformamidine-2'-deoxyadenosine-3'-diisopropylaminocyanoethyl phosphoramidite 
• 144490-31-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite 
• 118380-84-0 N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)cytidine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 129077-27-6 C₅₁H₅₉N₅O₉P 
• 130518-76-2 2',3'-O-dibenzoyl-3-undecyluridine 5'-<(2-cyanoethyl) diisopropylamino phosphite> 
• 130518-74-0 2',3'-O-dibenzoyl-3-<11-<(4-monomethoxytrityl)thio>undecyl>uridine 5'-<(2-cyanoethyl) diisopropylamino phosphite> 
• 130472-50-3 1-O-<(tert-butyl)dimethylsilyl>-3-O-<(2-cyanoethoxy)(N,N-diisopropylamino)phosphino>-2-deoxy-α-D-ribofuranose 
• 131444-94-5 5'-O-(4-Methoxytrityl)-2'-deoxyribosylurea-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 110764-78-8 N4-Benzoyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-methyl cytidine-3'-O-(β-cyanoethyl N,N-diisopropylphosphoramidite) 
• 109389-33-5 5'-O-(4,4'-Dimethoxytrityl)-N⁴-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine 3'-O-<2-cyanoethyl-N,N-diisopropylphosphoramidite> 
• 110522-84-4 N⁴-isobutyryl-2'-deoxycytidine-3'-diisopropylaminocyanoethyl phosphoramidite 

Relevant articles and documents

83. Nucleotide Coupling in Reverse Micelles

Nucleotide coupling was investigated in reverse micelles formed by (cetyl)trimethylammonium bromide (CTAB), in hexane/pentan-1-ol.In particular, the coupling of 2'-deoxy-5'-O-methylcytidine 3'-O-phosphate, prepared by phosphoramidite chemistry, with 5'-amino-5'-deoxythymidine was studied in the presence of a H2O-soluble carbodiimide at w0 = 11 and 22 (w0 = /).The effect of w0 on the reaction rate was investigated.A solid-phase strategy was developed for the synthesis of 2'-deoxy-5'-O-methyl-cytidyl-(3'-5')-5'-amino-5'-deoxythymidine.The nucleotide coupling yielding the expected product occurred readily in reverse micelles, and this is discussed in connection with the micelle self-replication program.

Voriconazole phosphorylcholine ester inner salt intermediates, preparation method and method for preparing voriconazole phosphorylcholine ester inner salt

The invention relates to the field of pharmaceutical chemicals, and discloses a plurality of voriconazole phosphorylcholine ester inner salt intermediates, voriconazole phosphorylcholine ester inner salts and a preparation method thereof, and the preparation method specifically comprises the following steps: carrying out oxidation reaction on a compound as shown in a formula II to prepare a compound as shown in a formula IV; dissolving the intermediate shown in the formula IV in a reaction solvent, and controlling the temperature to react for a certain time; then adding a hydrolytic agent, and purifying to obtain a voriconazole phosphorylcholine ester inner salt intermediate V shown as a formula V; and preparing the voriconazole phosphorylcholine ester inner salt as shown in the formula I from the intermediate as shown in the formula V under the action of an acid-binding agent. The obtained intermediates are good in purity and high in yield; the finally prepared voriconazole phosphorylcholine ester inner salt finished product is high in yield, and the purity is up to 99.5% or above; the preparation method of the intermediate is simple and convenient to operate, mature, reliable, short in reaction route, easily available in raw materials and suitable for large-scale industrial production.

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.