ChemInform Abstract: Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring.

Jean M. J. Tronchet; Imre Kovacs; Michel Seman; Pierre Dilda; Erik De Clercq; Jan Balzarini

doi:10.1002/chin.200044228

ChemInform Abstract: Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring.

ChemInform ◽

10.1002/chin.200044228 ◽

2000 ◽

Vol 31 (44) ◽

pp. no-no

Author(s):

Jean M. J. Tronchet ◽

Imre Kovacs ◽

Michel Seman ◽

Pierre Dilda ◽

Erik De Clercq ◽

...

Keyword(s):

Stereoselective Synthesis ◽

Biological Properties ◽

Oxirane Ring ◽

Nucleoside Analogues

Download Full-text

Highly Stereoselective Synthesis and Biological Properties of Nucleoside Analogues Bearing a Spiro Inserted Oxirane Ring

Nucleosides Nucleotides & Nucleic Acids ◽

10.1080/15257770008035024 ◽

2000 ◽

Vol 19 (4) ◽

pp. 775-794 ◽

Cited By ~ 7

Author(s):

Jean M. J. Tronchet ◽

Imre Kovacs ◽

Michel Seman ◽

Pierre Dilda ◽

Erik De Clercq ◽

...

Keyword(s):

Stereoselective Synthesis ◽

Biological Properties ◽

Oxirane Ring ◽

Nucleoside Analogues

Download Full-text

Photoredox-Catalyzed Stereoselective Synthesis of C-Nucleoside Analogues from Glycosyl Bromides and Heteroarenes

ACS Catalysis ◽

10.1021/acscatal.1c02088 ◽

2021 ◽

pp. 9397-9406

Author(s):

Liwen Xia ◽

Wenjing Fan ◽

Xiang-Ai Yuan ◽

Shouyun Yu

Keyword(s):

Stereoselective Synthesis ◽

Nucleoside Analogues

Download Full-text

Regio- and Stereoselective Synthesis of C-4′ Spirocyclobutyl Ribofuranose Scaffolds and Their Use as Biologically Active Nucleoside Analogues

Organic Letters ◽

10.1021/acs.orglett.1c03334 ◽

2021 ◽

Author(s):

Lucile Jouffroy ◽

Jonas Verhoeven ◽

Marta Brambilla ◽

Guido Verniest ◽

Hanchu Kong ◽

...

Keyword(s):

Stereoselective Synthesis ◽

Biologically Active ◽

Nucleoside Analogues

Download Full-text

ChemInform Abstract: Stereoselective Synthesis of 4′-Benzophenone-Substituted Nucleoside Analogues: Photoactive Models for Ribonucleotide Reductases.

ChemInform ◽

10.1002/chin.199720201 ◽

2010 ◽

Vol 28 (20) ◽

pp. no-no

Author(s):

T. E. LEHMANN ◽

A. BERKESSEL

Keyword(s):

Stereoselective Synthesis ◽

Nucleoside Analogues ◽

Ribonucleotide Reductases

Download Full-text

Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Pyrimidine C-Nucleoside Analogues

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20040918 ◽

2004 ◽

Vol 69 (4) ◽

pp. 918-932 ◽

Cited By ~ 4

Author(s):

Michal Šála ◽

Hubert Hřebabecký ◽

Milena Masojídková ◽

Antonín Holý

Keyword(s):

Sodium Salt ◽

Ring Opening ◽

Diethyl Malonate ◽

Oxirane Ring ◽

Nucleoside Analogues

The oxirane ring opening of 3-[(benzyloxy)methyl]-7-oxabicyclo[4.1.0]heptane with sodium salt of diethyl malonate followed by treatment with TsOH gave (3aR*,6R*,7aS*)-6-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3a) and (3aR*,5R*,7aS*)-5-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3b). Lactones 3a and 3b were formylated and then treated with thiourea or guanidine to give, after deprotection, racemic 5-[2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexyl]-2-thiouracil (5a and 5b) or -isocytosine (12a and 12b). Simple transformations of the 2-thiouracil derivative led to uracil (7a and 7b), 4-thiouracil (9a and 9b), and cytosine derivatives (10a and 10b).

Download Full-text