Syntheses of trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-trimethylsiloxyl carboxylates and N-trifluoroacetyl-2,3-didehydroamino acids

Chin. J. Org. Chem. ›› 1992, Vol. 12 ›› Issue (3): 294-297. Previous Articles Next Articles

Original Articles

2-(N-三氟乙酰-N-三甲基硅烷基)氨基-3-三甲基硅烷氧基-羧酸三甲基硅烷酯和2-(N-三氟乙酰)-2,3-脱氢氨基酸的合成

李增春;G. SIMCHEN

内蒙古民族师范学院化学系;斯图加特大学有机化学研究所;斯图加特大学生物化学研究所;斯图加特大学同位素研究所

发布日期:1992-06-25

Syntheses of trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-trimethylsiloxyl carboxylates and N-trifluoroacetyl-2,3-didehydroamino acids

LI ZENGCHUN;G. SIMCHEN

Published:1992-06-25

Abstract

The synthesis are described of 2-(N-trifluoroacetylamino-N-trimethylsilyl)-1,1-bis(trimethylsiloxy)ethene (I), trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl)amino-3-(trimethylsiloxy) carboxylates erythro- and threo-F3CCON(SiMe3)CH(CO2SiMe3)CHROSiMe3 (II; R = Ph, 4-MeOC6H4, Et, 3-ClC6H4, Et, 3-ClC6H4, 4-MeC6H4), and N-trifluoroacetyldidehydroamino acids (E)-, and (Z)-F3CCONHC(CO2H):CHR (III; R = Ph, 4-MeOC6H4, Et, 3-ClC6H4). N-Trifluoroacetylglycine is silylated by trimethylsilyl triflate in the presence of triethylamine to yield I. Reaction of aliphatic and aromatic aldehydes with I under the catalysis of zinc bromide affords II. Elimination of trimethylsilanol from II with trifluoromethansulfonic acid or I and treating the reaction mixture with saturated ammonium chloride solution then yielded III.

Key words: CARBOXYLIC ACID ESTER, AMINO ACID, SILANE P, SULFONIC ACID ESTER, TRIFLUOROACETIC ACID P

CLC Number:

O621

Cite this article

LI ZENGCHUN;G. SIMCHEN. Syntheses of trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-trimethylsiloxyl carboxylates and N-trifluoroacetyl-2,3-didehydroamino acids[J]. Chin. J. Org. Chem., 1992, 12(3): 294-297.

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2-(N-三氟乙酰-N-三甲基硅烷基)氨基-3-三甲基硅烷氧基-羧酸三甲基硅烷酯和2-(N-三氟乙酰)-2,3-脱氢氨基酸的合成

Syntheses of trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-trimethylsiloxyl carboxylates and N-trifluoroacetyl-2,3-didehydroamino acids

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