121373-20-4

Basic information

• Product Name: Bis(2-(trimethylsilyl)ethyl) diisopropylphosphoramidite
• Synonyms: Bis(2-(trimethylsilyl)ethyl) diisopropylphosphoramidite;iPr2N-P-(OTSE)2;Bis[2-(trimethylsilyl)ethyl] N,N-diisopropylphosphoramidite;Bis[2-(trimethylsilyl)ethyl] N,N-diisopropylphosphoramidite 96%;bis-[2-(trimethylsiyl)ethoxy]-N,N-diisopropylamidophosphine
• CAS NO: 121373-20-4
• Molecular Formula: C₁₆H₄₀NO₂PSi₂
• Molecular Weight: 365.65
• Mol File: 121373-20-4.mol

Chemical Properties

• Boiling Point: 286.2-296.6°C
• Flash Point: >110℃
• Appearance: /
• Density: 0.8887 g/mL at 25 °C
• Refractive Index: n20/D1.4517
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Bis(2-(trimethylsilyl)ethyl) diisopropylphosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-(trimethylsilyl)ethyl) diisopropylphosphoramidite(121373-20-4)
• EPA Substance Registry System: Bis(2-(trimethylsilyl)ethyl) diisopropylphosphoramidite(121373-20-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 121373-20-4(Hazardous Substances Data)

Usage

Uses

Phosphitylation agent used in the preparation of oligonucleotides

Upstream product

• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 108-18-9 diisopropylamine 

Downstream Products

• 1197420-26-0 (R)-2-(4-(6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy)-1-cyclopropylethyl bis(2-(trimethylsilyl)ethyl)phosphate 
• 158817-09-5 N^α-(9-fluorenylmethyloxycarbonyl)-O-phosphono>tyrosine 
• 1026872-20-7 Phosphorous acid 1-methyl-3-phenyl-propyl ester bis-(2-trimethylsilanyl-ethyl) ester 

Relevant articles and documents

N,N-diisopropyl-bis[2-(trimethylsilyl)ethyl]phosphoramidite. An attractive phosphitylating agent compatible with the Fmoc/t-butyl strategy for the synthesis of phosphotyrosine containing peptides

A new phosphitylating agent, compatible with the Fmoc/t-butyl strategy for the production of phosphotyrosine containing peptides was synthesized. Our results demonstrated that high yields and high purities of phosphotyrosine peptides can be obtained using this phosphitylating agent.

Identification of a nonbasic melanin hormone receptor 1 antagonist as an antiobesity clinical candidate

Identification of MCHR1 antagonists with a preclinical safety profile to support clinical evaluation as antiobesity agents has been a challenge. Our finding that a basic moiety is not required for MCHR1 antagonists to achieve high affinity allowed us to explore structures less prone to off-target activities such as hERG inhibition. We report the SAR evolution of hydroxylated thienopyrimidinone ethers culminating in the identification of 27 (BMS-819881), which entered obesity clinical trials as the phosphate ester prodrug 35 (BMS-830216).

HYDROXY SUBSTITUTED THIENO PYRIMIDINONES AS MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS

The present invention provides compounds having the following Formula IA and IB, which are useful as MCHR1 antagonists, and includes prodrugs and pharmaceutically acceptable salts thereof:

Synthesis of combretastatin A-4 prodrugs and trans-isomers thereof

The present invention relates to novel water-soluble, stable derivatives of combretastatin A-4, and novel synthesis methods therefore. The combretastatin A-4 prodrugs described herein appear to be useful in the treatment of neoplastic disease.

Use of Bis N,N-Dialkylphosphoramidites for the Synthesis of Phosphate Monoesters

The bis N,N-dialkylphosphoramidites 7a and b and bis N,N-dialkylphosphoramidites 6a and b have been prepared by reaction of the N,N-dialkylphosphorochloridites 5a and b with the appropriate 2-(trialkylsilyl)ethanol.In the presence of 1H-tetrazole, the phosphoramidites 6a, b and 7a, b phosphorylated MeOH, PhCH2OH, PhCH2CH2OH, Me(PhCH2CH2(CHOH, 2,3,4,5,6-penta-O-benzyl-myo-inositol and ButOH, to give the phosphites 8a-h.Without isolation, these were oxidized to the corresponding phosphate triesters 9a-h with m-chloroperbenzoic acid.Treatment of the triesters 9a-h with tetrabutylammonium fluoride removes only 2-(trialkylsilyl)ethyl group to give the diesters 10a-h, whereas treatment with a solution of hydrofluoric acid in acetonitrile-water gives the phosphate monoesters 11a-e.

Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis

Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis.The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined.On the basis of these data, the bis-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO3MDPSE2)-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides.The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.