203738-69-6

Basic information

• Product Name: TERT-BUTYL 2-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYLCARBAMATE
• Synonyms: TERT-BUTYL 2-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYLCARBAMATE
• CAS NO: 203738-69-6
• Molecular Formula: C₁₃H₂₉NO₃Si
• Molecular Weight: 275.46
• Mol File: 203738-69-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 312.909 °C at 760 mmHg
• Flash Point: 143.042 °C
• Appearance: /
• Density: 0.925
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: TERT-BUTYL 2-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 2-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYLCARBAMATE(203738-69-6)
• EPA Substance Registry System: TERT-BUTYL 2-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYLCARBAMATE(203738-69-6)

Safety Data

• Hazardous Substances Data: 203738-69-6(Hazardous Substances Data)

Usage

General Description

Tert-Butyl 2-(tert-butyldimethylsilyloxy)ethylcarbamate is a chemical compound that is commonly used in organic synthesis and as a protecting group for amines. It is a derivative of tert-butyl carbamate and contains a tert-butyldimethylsilyloxy group as a protecting group for the carbamate functionality. This chemical is often utilized in the protection of amines during organic reactions to prevent unwanted side reactions and to facilitate the synthesis of complex organic molecules. It is a versatile compound that plays an important role in the development of pharmaceuticals, agrochemicals, and other fine chemicals.

InChI:InChI=1/C13H29NO3Si/c1-12(2,3)17-11(15)14-9-10-16-18(7,8)13(4,5)6/h9-10H2,1-8H3,(H,14,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant articles and documents

Synthesis and Evaluation of Radiolabeled Phosphoramide Mustard with Selectivity for Hypoxic Cancer Cells

Tumor hypoxia has been widely explored over the years as a diagnostic and therapeutic marker. Herein, we synthesized an alkyne functionalized version of evofosfamide, a hypoxia-selective prodrug. The purpose of this effort was to investigate if this novel 2-nitroimidazole phosphoramide nitrogen mustard (2-NIPAM) retained hypoxia selectivity and could be utilized in radiopharmaceutical development to significantly increase retention of conjugated agents in hypoxic cells. 2-NIPAM demonstrated good hypoxia selectivity with a 62- and 225-fold increase in cytotoxicity toward PC-3 and DU145 human prostate cancer cell lines, respectively, under hypoxic conditions. Radiolabeling of 2-NIPAM with 125I was accomplished through a Cu(I)-mediated azide-alkyne cycloaddition reaction. The 125I-conjugate demonstrated 13.6 and 17.8% lower efflux rates for DU145 and PC-3 cells, correspondingly, under hypoxic conditions, suggesting that the increased retention is likely due to the known intracellular trapping mechanism. In conclusion, these studies demonstrate the potential of 2-NIPAM in serving as a trapping agent for radiopharmaceutical development.

Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols

An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza-)alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds have been compared. I

Vinyl dihydropyrans and dihydrooxazines: Cyclizations of catalytic ruthenium carbenes derived from alkynals and alkynones

A novel synthesis of 2-vinyldihydropyrans and dihydro-1,4-oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles. Mechanistic aspects of the new cyclizations are discussed. Setting a trap: A novel synthesis of 2-vinyldihydropyrans and dihydro-1,4-oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles.