Synthesis of (3S,4S)-4-Acetyl-3-(1R)-1-hydroxyethyl-1-(4-methoxyphenyl)azetidin-2-one

被引：1

作者：

Selezneva, N. K. ^{[1
]}

Galeeva, A. M. ^{[1
]}

Valiullina, Z. R. ^{[1
]}

Miftakhov, M. S. ^{[1
]}

机构：

[1] Ufa Inst Chem, Russian Acad Sci, Ufa Fed Res Ctr, Ufa 450054, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 58卷 / 11期

关键词：

2-bromo-3-hydroxybutanamides; beta-methallyl chloride; N-alkylation; ozonolysis; intramolecular epoxide-enolate cyclization; azetidin-2-ones; CARBAPENEMS;

D O I：

10.1134/S1070428022110203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the title compound from l-threonine with the participation of beta-methallyl chloride amide in the N-alkylation step is described.

引用

页码：1676 / 1679

页数：4

共 12 条

[1] Preparations of two pivotal intermediates for the synthesis of 1-beta-methyl carbapenem antibiotics [J].

Berks, AH .

TETRAHEDRON, 1996, 52 (02) :331-375

[2] Preparation of β-lactams by [2+2] cycloaddition of ketenes and imines [J].

Fu, Nanyan ;

Tidwell, Thomas T. .

TETRAHEDRON, 2008, 64 (46) :10465-10496

[3] A practical preparation of the key intermediate for penems and carbapenems synthesis [J].

Grzeszczyk, Barbara ;

Stecko, Sebastian ;

Mucha, Lukasz ;

Staszewska-Krajewska, Olga ;

Chmielewski, Marek ;

Furman, Bartlomiej .

JOURNAL OF ANTIBIOTICS, 2013, 66 (03) :161-163

[4] Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide [J].

Hosseini, Abolfazl ;

Schreiner, Peter R. .

ORGANIC LETTERS, 2019, 21 (10) :3746-3749

[5] Synthesis of (1′R,3S,4S)-3-[1′-(tert-butyldimethylsilyloxy)ethyl]-4-(cyclopropylcarbonyloxy)azetidin-2-one [J].

Laurent, Mathieu ;

Ceresiat, Marcel ;

Marchand-Brynaert, Jacqueline .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3755-3766

[6] Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue [J].

Selezneva, Natalya K. ;

Valiullina, Zuleykha R. ;

Khasanova, Lidiya S. ;

Gimalova, Fanuza A. ;

Biglova, Raisa Z. ;

Miftakhov, Mansur S. .

MENDELEEV COMMUNICATIONS, 2018, 28 (02) :131-132

[7] STEREOSPECIFIC SYNTHESIS OF D-ISOTHREONINE FROM L-THREONINE [J].

SHIMOHIGASHI, Y ;

WAKI, M ;

IZUMIYA, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (03) :949-950

[8] Kinugasa reaction: an 'ugly duckling' of β-lactam chemistry [J].

Stecko, Sebastian ;

Furman, Bartlomiej ;

Chmielewski, Marek .

TETRAHEDRON, 2014, 70 (43) :7817-7844

[9] Enantioenriched γ-Aminoalcohols, β-Amino Acids, β-Lactams, and Azetidines Featuring Tetrasubstituted Fluorinated Stereocenters via Palladacycle-Catalyzed Asymmetric Fluorination of Isoxazolinones [J].

Wannenmacher, Nick ;

Pfeffer, Camilla ;

Frey, Wolfgang ;

Peters, Rene .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01) :670-682

[10] Overcoming Resistance to β-Lactam Antibiotics [J].

Worthington, Roberta J. ;

Melander, Christian .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09) :4207-4213

← 1 2 →