125486-96-6 Usage
Uses
Used in Organic Synthesis:
2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% is used as a reagent for the introduction of a SES-protected nitrogen functionality, which can be cleaved with fluoride ion. This property makes it a valuable tool in organic synthesis, allowing for the protection and manipulation of nitrogen-containing compounds.
Used in Preparation of N-Sulfonylimines:
2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% is used as a source of nucleophilic nitrogen that can react with electrophiles to form N-sulfonylimines. These compounds are important intermediates in the synthesis of various organic molecules, including pharmaceuticals and natural products.
Used in Mitsunobu Reactions:
2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% is utilized in Mitsunobu reactions, which are a class of organic reactions that involve the inversion of stereochemistry at a stereocenter. The use of 2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% in these reactions allows for the selective protection and manipulation of nitrogen-containing substrates.
Used in Azaglycosylation Chemistry:
2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% is employed in azaglycosylation chemistry, a process that involves the formation of nitrogen-containing sugar analogs. These analogs are important in the synthesis of various biologically active compounds, including glycoconjugates and glycoproteins.
Used in Preparation of Sulfodiimides:
This reagent is used in the preparation of sulfodiimides, which are key intermediates in the synthesis of various nitrogen-containing heterocycles and pharmaceuticals.
Used in Preparation of (N-SES-imino)phenyliodinane:
2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90% is utilized in the preparation of (N-SES-imino)phenyliodinane, a versatile reagent in organic synthesis that can be used for the formation of carbon-nitrogen bonds and the cyclization of various substrates.
Preparation
2-(Trimethylsilyl)ethanesulfonamide is prepared by reaction of 2-(trimethylsilyl)
ethanesulfonyl chloride (accessible from the commercially
available sodium salt of the corresponding sulfonic acid or starting
from vinyl trimethylsilane) with gaseous ammonia (eq 1).
Check Digit Verification of cas no
The CAS Registry Mumber 125486-96-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,5,4,8 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 125486-96:
(8*1)+(7*2)+(6*5)+(5*4)+(4*8)+(3*6)+(2*9)+(1*6)=146
146 % 10 = 6
So 125486-96-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H15NO2SSi/c1-10(2,3)5-4-9(6,7)8/h4-5H2,1-3H3,(H2,6,7,8)
125486-96-6Relevant articles and documents
A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)
Parker, Laurie L.,Gowans, Nicholas D.,Jones, Stephen W.,Robins, David J.
, p. 10165 - 10171 (2003)
SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles.
Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine
Benohoud, Meryem,Leman, Loic,Cardoso, Silvia H.,Retailleau, Pascal,Dauban, Philippe,Thierry, Josiane,Dodd, Robert H.
supporting information; experimental part, p. 5331 - 5336 (2009/12/03)
(Chemical Equation Presented) The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers wa
Sequential aza-Baylis-Hillman/ring closing metathesis/aromatization as a novel route for the synthesis of substituted pyrroles
Declerck, Valerie,Ribiere, Patrice,Martinez, Jean,Lamaty, Fredereric
, p. 8372 - 8381 (2007/10/03)
A new route to diverse 2-substituted-3-methoxycarbonyl pyrroles has been developed. Diverse SES protected α-methylene β-aminoesters were obtained by a 3-component aza-Baylis-Hillman reaction. Diversity arose from the aryl aldehydes which can be used in th
Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: Use of phenyldiazomethane, diazoesters and diazoacetamides
Aggarwal,Ferrara,O'Brien,Thompson,Jones,Fieldhouse
, p. 1635 - 1643 (2007/10/03)
Imine aziridination using diazo-compounds and catalytic quantities of metal salts and sulfides has been investigated. A range of imines derived from benzaldehyde bearing electron-withdrawing groups (N-Ts,N-SO2CH2CH2SiMesu
