56183-63-2

Usage

Uses

Used in Pharmaceutical Industry:
Bis(diisopropylamino)chlorophosphine is used as a reagent in the synthesis of tert-butyl tetraisopropylphosphorodiamidite ligand for palladium-catalyzed Buchwald-Hartwig amination reaction. This reaction is crucial for the production of various pharmaceutical compounds, as it allows for the formation of carbon-nitrogen bonds, which are essential in the construction of complex organic molecules.
Used in Catalyst Synthesis:
In the field of catalysis, Bis(diisopropylamino)chlorophosphine is used as a precursor to synthesize acyclic N-phosphonio imine catalysts. These catalysts are employed in selective epoxidations, a type of chemical reaction that is vital for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Organophosphorus Chemistry:
Bis(diisopropylamino)chlorophosphine is also utilized in the synthesis of boryl-substituted methylenephosphonium derivatives. These derivatives are valuable intermediates in organophosphorus chemistry, which has applications in various industries, including the production of specialty chemicals, materials, and pharmaceuticals.

Upstream product

• 109065-32-9 (chloro)diazomethylenephosphorane 
• 97135-48-3 (bis(diisopropylamino)phosphanyl)(trimethylsilyl)diazomethane 
• 80907-47-7 {NEt₄}{HW(CO)5} 
• 117270-09-4 ({(CH₃)2CH}2N)2PPCl₂ 
• 113533-22-5 C--N-nitrilimine 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 108-18-9 diisopropylamine 

Downstream Products

• 92611-10-4 bis(N,N-diisopropylamino)methoxyphosphine 
• 106892-37-9 C₄₀H₇₂N₄O₄P₄ 
• 131853-35-5 5'-O-(4,4'-dimethoxytrityl)-N³-benzoylthymidine 3'-N,N-diisopropylphosphonoamidate 
• 106892-35-7 C₅₀H₇₆N₄O₂P₄ 
• 121238-14-0 C₅₀H₆₄N₅O₇P 
• 104655-85-8 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N,N-diisopropyl-H-phosphonamidate 
• 104655-84-7 5‘-O-dimethoxytrityl-2’-deoxyribothymidine 3‘-O-phosphorodiamidite 
• 120362-95-0 Cyanbis(diisopropylamino)phosphonio(triphenylphosphoranyliden)methan 
• 68880-43-3 C₁₂H₂₈N₂P⁽¹⁺⁾ 
• 104655-82-5 5'-O-(p,p'-dimethoxytrityl)thymidine 3'-(allyl N,N-diisopropylphosphoramidite) 
• 98796-52-2 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[4-(2-methyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 98796-51-1 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine-3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite] 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 135961-76-1 bis(diisopropylamino)(phenylimino)phosphinic chloride 

Relevant academic research and scientific papers

N-Phosphino- and N-Phosphonionitrilimines: From Nucleophilic to Electrophilic 1,3-Dipoles

N-[Bis(diisopropylamino)phosphino]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (1) reacts with electron-poor dipolarophiles such as maleimide, methyl vinyl ketone, and 1,4-naphthoquinone via HOMO(dipole)-controlled [2+3] cycloadditions, while N-[bis(diisopropylamino)(methyl)phosphonio]-C-[bis(diisopropylamino) thioxophosphoranyl]nitrilimine (2a) reacts with electron-rich dipolarophiles such as norbornadiene and ethyl trans-pyrrolineacrylate via LUMO(dipole)-controlled [2+3] cycloadditions. Carbon disulfide reacts with 1 via a formal [4+2] cycloaddition leading to phosphazene containing heterocycle 11 in 75% yield. Dipole 1 is cleaved by HCl, giving the corresponding (thioxophosphoranyl)diazomethane 15, while addition of HCl to 2a leads to hydrazonoyl chloride 16, in 70% isolated yield. Hydrazone 17′ (95%) and phosphazine 18 (80%) are obtained by a 1,3-addition of BuLi to 1 and PhOLi to 2a, respectively. Trimethylphosphine reacts with 2a by a phosphine - carbene coupling reaction, giving the ylide 20 which is isolated in 75% yield.

Synthesis and properties of di-isopropylamino derivatives of diphosphanes and triphosphanes: The x-ray structure of (ipr2n) 2p-p(sime3)2

(iPr2N)2PCl (3) reacts with P(SiMe 3)2Li yielding crystalline (iPr2N) 2P-P(SiMe3)2 (1). Compound 1 crystallizes in the orthorhombic space group Pbca. The lithiation of 1 with BuLi yields ( iPr2N)2P-P(SiMe3)Li (2). Compound 2 reacts with 3 with the formation of (iPr2N) 2P-P(SiMe3)-P(NiPr2)2 (4) in high yield. Attempts to lithiate 4 with BuLi in THF solution in order to obtain (iPr2N) 2P-PLi-P(NiPr2) 2were unsuccessful, probably due to strong electron donation of the iPr2N groups into the P-P-P skeleton in 4.

BULKY ALKYLS, AMIDES, AND ARYLOXIDES OF MAIN GROUP 5 ELEMENTS. PART 1. PERSISTENT PHOSPHINYL AND ARSINYL RADICALS MRR' AND THEIR CHLOROPRECURSORS MRR'Cl AND RELATED COMPOUNDS

Interaction of LiR and MCl3 in appropriate stoicheiometry affords the following new compounds: MCl2 or M2Cl (M = P, As, or Sb), MCl2 or M2Cl (M = As or Sb), or Bi3.Reaction of P(NPri2)Cl2 with Li*OEt2, Li, Li, MgButBr, or NHPri2 yields the corresponding new compound P(NPri2)RCl, while Li with P(NMe2)Cl2 affords P(NMe2)Cl.Reduction of the appropriate phosphorus(III) or arsenic(III) monochloride in toluene by photolysis with the olefin gives the persistent (t1/2 = 3 days to > 1 year in PhMe at 300 K) phosphorus(II) or arsenic(II) alkyl or amide: M2 (M = P or As), M2, P(NR2) (R = Pri or SiMe3), P(NPri2),P2, or P(NPri2).Electron spin resonance parameters are discussed.

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.

Self-neutralizing oligonucleotides with enhanced cellular uptake

There is tremendous potential for oligonucleotide (ON) therapeutics, but low cellular penetration due to their polyanionic nature is a major obstacle. We addressed this problem by developing a new approach for ON charge neutralization in which multiple branched charge-neutralizing sleeves (BCNSs) are attached to the internucleoside phosphates of ON by phosphotriester bonds. The BCNSs are terminated with positively charged amino groups, and are optimized to form ion pairs with the neighboring phosphate groups. The new modified ONs can be prepared by standard automated phosphoramidite chemistry in good yield and purity. They possess good solubility and hybridization properties, are not involved in non-standard intramolecular aggregation, have low cytotoxicity, adequate chemical stability, improved serum stability, and above all, display significantly enhanced cellular uptake. Thus, the new ON derivatives exhibit properties that make them promising candidates for the development of novel therapeutics or research tools for modulation of the expression of target genes.

Stereoselective P-Cyclisation and Diastereoisomeric Purification of 5-Phenyl-3-(pyridin-2-yl)-1,3,2-oxazaphospholidine Formed from a Thermolabile Protecting Group

A one-pot, two-step synthesis of 5-phenyl-3-(pyridin-2-yl)-1,3,2-oxazaphospholidine from linear precursor bis(diisopropylamino){2-[(pyridin-2-yl)amino]-1-phenylethoxy}phosphine is achieved using a stereoselective intramolecular cyclisation. Application of a pure enantiomer {1-phenyl-2-[(pyridin-2-yl)amino]ethanol} enabled partial diastereopurification by crystallisation. For all four diastereoisomers, the absolute configuration of the P-centre was determined using X-ray crystallography and correlative 31P NMR data. Stereochemically pure 5a was then used in nucleoside phosphitylation reactions with partial loss of stereopurity by retention of configuration on the phosphorus centre. A one-pot, two-step synthesis of 5-phenyl-3-(pyridin-2-yl)-1,3,2-oxazaphospholidine from linear bis(diisopropylamino){2-[(pyridin-2-yl)amino]-1-phenylethoxy}phosphine by stereoselective intramolecular P-cyclisation is described. For all four diastereoisomers produced, the absolute configuration of the P-centre is determined by X-ray crystallography and correlated with 31P NMR data.

NEW METHOD OF POLYPHOSPHATE SYNTHESIS

The subject of the invention is a new method of the synthesis of polyphosphate analogues, such as nucleosides, oligonucleotides, carbohydrates, peptides and proteins, which are of biological importance and are used in organic chemistry, molecular biology and biotechnology. Polyphosphate analogues, including in particular nucleoside 5'-triphosphates, display high biological activity and are responsible for the provision and storage of energy in live organisms. The method relates to the synthesis of organic polyphosphates of general formula (1), where n has a value of 0 to 2, while X stands for an organic radical, in particular nucleoside, oligonucleotide, peptide-carbohydrate or a protein radical.

Solid-phase synthesis of 5′-O-β,γ-methylenetriphosphate derivatives of nucleosides and evaluation of their inhibitory activity against HIV-1 reverse transcriptase

Bis(dichlorophosphino)methane was converted to a β,γ-methylenetriphosphitylating reagent. The reagent was immobilized on aminomethyl polystyrene resin-bound linker of 4-acetoxy-3-phenylbenzyl alcohol to afford a polymer-bound β,γ-methylenetriphosphitylating reagent, which was reacted with unprotected nucleosides followed by oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and acidic cleavage to produce 5′-O-β,γ-methylene triphosphate nucleosides in 53-82% overall yields. Among all the compounds, cytidine 5′-O-β,γ-methylenetriphosphate inhibited completely RNase H activity of HIV-1 reverse transcriptase at 700 μM.

Optimized synthesis of phosphatidylserine

The synthesis of phosphatidyl serine containing saturated fatty acids was thoroughly studied and optimized in order to establish a protocol amenable to large-scale synthesis. The key step was a one-pot multicomponent reaction involving an O-benzyl phosphorodiamidite, protected serine and diacylglycerol, followed by in situ oxidation of the resulting phosphite. In order to replace expensive and poorly stable tetrazole, a screening of substitutes was carried out and imidazolium chloride was selected as the best suited one. Springer-Verlag 2010.

Protecting of a thermolabile protecting group: "click-clack" approach

Image Presented A new method for attaining higher stability of thermolabile protecting groups (TPG) using an intramolecular cyclization through a "click-clack" approach was demonstrated. It was found that during intramolecular cyclization of 2-pyridyl typ