5630-82-0

Upstream product

• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 56-40-6 glycine 
• 23728-68-9 N-Methyl-N-(trimethylsilyl)benzamide 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 

Downstream Products

• 107222-84-4 6-Amino-3-O-benzyl-6-desoxy-1,2-O-isopropyliden-D-glycero-α-D-gluco-heptofuranuronsaeure 
• 107222-83-3 6-Amino-3-O-benzyl-6-desoxy-1,2-O-isopropyliden-L-glycero-β-L-ido-heptofuranuronsaeure 

Relevant academic research and scientific papers

29Si and 13C NMR Spectra of Trimethylsilylated Amino Acids

The 29Si and 13C NMR chemical shifts are reported for trimethylsilyl derivatives of 25 amino acids, the majority of which occur naturally as protein constituents of foodstuffs.The 29Si chemical shifts in trimethylsilyl esters of amino acids roughly correlate linearly with the pK values of the parent amino acid.No such simple correlations were found for the shifts in the fully trimethylsilylated amino acids.The 29Si chemical shifts of various functionalities encountered fall into distinct spectral regions, but the shifts of (CH3)3SiN or (CH3)3SiOOC groups alone are not sufficiently characteristic to identify the acid but their combination is in most cases. - Keywords: 29Si NMR 13C NMR Amino acids Trimethylsilyl derivatives Chemical shifts pK values

CONTRIBUTIONS TO THE CHEMISTRY OF ORGANIC SILICON-NITROGEN-COMPOUNDS, I. SYNTHESIS OF N,N-BIS-(TRIMETHYLSILYL)AMINES

The preparation of N,N-bis-(trimethylsilyl)amines 1 has been investigated.Three convenient methods are reported: A, Transfer of (catalytically) activated Tms-groups to amines starting from N-silylated carbonamides, B, silylation of amines with trimethylsilylchloride 5/NEt3 in the presence of TiCl4, C, silylation of primary amines 4 or mono-(trimethylsilyl)amines 16 with CF3SO3 Tms/NEt3 or TmsI/NEt3.Methods A and B are limited to the silylation of (ar)alkylamines which have no branched α-position. Key words: N,N-bis-(trimethylsilyl)amines; N,N-bis-silylamines; N-silylcarbonamides.

N-bis-silylation of α-amino acids: "benzostabases" as amino protecting group

N-Bis-trimethylsilylation of α-amino acids using the powerful trimethylsilyl triflate reagent is difficult, and is rendered impossible in the case of bulky side-chains (valine). However, favorable entropy changes resulting from a cyclization reaction allow the formation of "benzostabase" N-diprotections regardless of the side-chain bulk.

Branched and Chain-Extended Sugars, XXXI. - Synthesis of the Deferri Form of the Oxygen Analogue of &δ1-Albomycin

The oxygen analogue of the deferri form of δ1-albomycin has been synthesized.Reaction of the xylo-dialdehyde 2 with the anion of the lithium salt 3 of N,N-bis(trimethylsilyl)glycine trimethylsilyl ester leads to the chain-extended sugar.In good stereochemical selectivity the desired 6-amino-6-desoxy-L-ido-hepturonic acid is isolated as derivative 8.After transformation of 8 into the 1-acetate 23 the nucleoside 26 is obtained by a modification of the Hilbert-Johnson reaction using the uracil derivative 24.N-Methylation of 26 gives 28 in good yield.The serine derivative 31 reacts with the deblocked amino compound 30 to yield the peptide nucleoside 32.The tripeptide 36, which contains three units of N5-acetyl-N5-hydroxyl-L-ornithine, is successfully linked to the partial deblocked compound 34 via the mixed carbonic anhydride method.Final hydrogenation of 37 gives the free deferri form of the oxygen analogue 38.

SYNTHESIS OF α-AMINO-β-HYDROXY ACIDS USING KETENE BIS(TRIMETHYLSILYL) ACETAL OR ITS N-METHYL-N-TRIMETHYLSILYL ANALOG

Condensation of the title compounds with aldehydes and ketones in the presence of trimethylsilyl triflate provided the correspondig α-amino-β-hydroxy acids in fair to good yields as a mixture of diastereomers.