67746-43-4

Usage

Uses

Used in Organic Synthesis:
Dibenzyl diethylphosphoramidite is used as a phosphitylating reagent for the synthesis of glycosyl phosphites and phosphates. It plays a crucial role in the preparation of these compounds, which are essential building blocks in the synthesis of complex organic molecules, including oligosaccharides.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, dibenzyl diethylphosphoramidite is used for the phosphorylative conversion of alcohols into their corresponding dibenzylphosphorotriesters. This process is vital for the synthesis of various pharmaceutical compounds, as it allows for the introduction of a phosphorus-containing functional group, which can impart unique properties to the final product.
Used in Carbohydrate Chemistry:
Dibenzyl diethylphosphoramidite is used in carbohydrate chemistry as a reagent for the preparation of 6-dibenzylphosphate-1,3,5-tri-O-PMB-myo-inositol. DIBENZYL DIETHYLPHOSPHORAMIDITE is an important intermediate in the synthesis of various biologically active molecules, including those with potential therapeutic applications.
Overall, dibenzyl diethylphosphoramidite is a valuable reagent in various fields, including organic synthesis, pharmaceuticals, and carbohydrate chemistry, due to its ability to efficiently convert alcohols into their corresponding dibenzylphosphorotriesters and dibenzyl glycosyl phosphites, which can be further utilized in the synthesis of complex organic molecules and pharmaceutical compounds.

InChI:InChI=1/C18H24NO2P/c1-3-19(4-2)22(20-15-17-11-7-5-8-12-17)21-16-18-13-9-6-10-14-18/h5-14H,3-4,15-16H2,1-2H3

Upstream product

• 2283-11-6 hexaethylphosphoric triamide 
• 100-51-6 benzyl alcohol 
• 1069-08-5 diethylphosphoramidous dichloride 
• 39182-31-5 N,N-diethylphosphoramidous acid 
• 66954-57-2 benzyl tetraethylphosphorodiamidite 
• 109-89-7 diethylamine 

Downstream Products

• 26292-51-3 dibenzyl methyl phosphate 
• 1623-08-1 phosphoric acid dibenzyl ester 
• 97194-51-9 phosphoric acid benzyl ester-methyl ester 
• 620-05-3 iodomethylbenzene 
• 149717-36-2 dibenzyl 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl phosphite 
• 149717-35-1 Dibenzyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl phosphite 
• 374726-30-4 Acetic acid (2R,3R,4S,5S)-3,5-diacetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester 
• 75257-04-4 1,2-distearoylglycerol dibenzyl phosphite 
• 75257-03-3 Hexadecanoic acid 2-(bis-benzyloxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester 
• 374726-31-5 Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-2-(bis-benzyloxy-phosphanyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 144002-21-1 dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite 
• 134150-51-9 N²-<<(9H-Fluoren-9-yl)methoxy>carbonyl>-O⁴--L-tyrosine 
• 117666-33-8 Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3,4,5-tris-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester 
• 22433-84-7 Dibenzyl-tert.-butylphosphat 

Relevant academic research and scientific papers

Practical and scalable synthesis of α-(1→4)-linked polysaccharides composed of 6-O-methyl-D-glucose

A second-generation synthesis of synthetic 6-O-methyl-D-glucose-containing polysaccharides (sMGPs) is reported. Glycosidation acceptor A and donor B are prepared from α-, β-, and γ-cyclodextrins in high yields. The glycosidation of A and B, followed by de

Mild regioselective phosphorylation of β-cyclodextrin with trivalent phosphorus acid amides

Phosphorylation of β-cyclodextrin with trivalent phosphorus acid diamides in pyridine is found to proceed selectively at primary hydroxy groups under mild conditions (20°C) due to the supramolecular effect of the cyclodextrin cavity. The compounds obtained are of practical interest for further synthesis on their basis of amphiphilic glycophospholipids immobilized on the cyclodextrin matrix. Nauka/Interperiodica 2006.

Dismutation of arylene phosphorodiamidites: Specific features and aspects of preparative use

The dismutation of arylene phosphorodiamidites derived from the simplest phenols and naphthols and of their dibasic analogs was studied. The main regular trends of this process and the limits of its synthetic applicability were determined. Pleiades Publishing, Inc., 2006.

Dismutation of diamidoarylphosphites

Some examples of spontaneous dismutation of diamidoarylphosphites in different solvents were studied, and features of the process were revealed.

Synthesis of Casein-Related Peptides and Phosphopeptides. VII. The efficient Synthesis of Ser(P)-Containing peptides by the Use of Boc-Ser(PO3R2)-OH Derivatives

A new approach to the synthesis of Ser(PO3R2)-containing peptides by using five protected Boc-Ser(PO3R2)-OH (R = phenyl, ethyl, methyl, benzyl, t-butyl) derivatives is described.The five Boc-protected derivatives are prepared by a simple three-step synthe

An improved synthesis of dihydroxyacetone phosphate

An improved procedure has been developed for the synthesis of dihydroxyacetone phosphate (DHAP). Reaction of 2,5-diethoxy-p-dioxane-2,5-dimethanol (1) and the trivalent phosphorylating reagent dibenzyl-N,N-diethylphosphoramidite (DDP) in the presence of 1,2,4-triazole or tetrazole followed by oxidation with H2O2 gave 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-21-O-51-bis(phosphate) tetrabenzyl ester (2) in 98% yield. Compound 2 was then hydrogenated in the presence of H2-Pd/C to give, after neutralization, 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-21-O-51-bis(phosphate) as a stable trisodium salt (3) in 84% yield. Treatment of 3 with Dowex 50 (H+) generates 2 equivalents of DHAP.

Synthesis of Casein-Related Peptides and Phosphopeptides. V The Efficient Global 'Phosphite-Triester' Phosphorylation of Protected Serine Derivatives and Peptides by Using Dibenzyl or Di-t-butyl N,N-Diethylphosphoramidite.

Both dibenzyl N,N-diethylphosphoramidite and di-t-butyl N,N-diethylphosphoramidite are shown to be suitable reagents for the efficient 1H-tetrazole-catalysed 'phosphite-triester' phosphorylation of the protected serine derivative Boc-Ser-OCH2C6H4NO2-p. Bo

A NEW, CONVENIENT AND EFFICIENT GENERAL PROCEDURE FOR THE CONVERSION OF ALCOHOLS INTO THEIR DIBENZYL PHOSPHOROTRIESTERS USING N,N-DIETHYL DIBENZYL PHOSPHORAMIDITE

A general procedure is described for the near-quantitative preparation of alkyl dibenzyl phosphates by treating primary, secondary or tertiary alcohols with N,N-diethyl dibenzyl phosphoramidite/1H,5-methyltetrazole followed by mild oxidation of the resultant alkyl dibenzyl phosphites with 3-chloroperoxybenzoic acid.

A new approach to the synthesis of phosphatidic acids and their analogs

The synthesis of phosphatidic acids, their monoamides and dialkyl esters, and thiophosphatidic acids was realized on the basis of the amidophosphites of 1,2-diacylglycerols and 1,2-isopropylideneglycerol.