Handbook of Nucleoside Synthesis,9780471093831

Handbook of Nucleoside Synthesis

by ; ;
Edition: 1st
ISBN13: 9780471093831
ISBN10: 0471093831
Format: Paperback
Pub. Date: 2001-08-03
Publisher(s): Wiley-Interscience
List Price: $184.03

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Summary

Handbook of Nucleoside Synthesis includes descriptive information regarding the three principal types of nucleoside forming reactions: the Fusion Reaction, the Metal Salt Procedure, and the Hilbert-Johnson Reaction, as well as other miscellaneous methods.

Author Biography

HELMUT VORBRÜGGEN is Professor of Chemistry at the Free University in Berlin, Germany.

Table of Contents

Foreword vii
Preface ix
Acknowledgments xii
Synthesis of Nucleosides
1(1)
Introduction
1(3)
Scope and Limitations
2(1)
Sugar Moieties
3(1)
Nucleoside Synthesis
4(6)
The Fusion Reaction
4(1)
The Metal Salt Procedure
4(4)
The Classical Hilbert-Johnson Procedure for the Preparation of Pyrimidine Nucleosides
8(2)
The Silyl-Hilbert-Johnson Reaction
10(1)
Silyl-Hilbert-Johnson Reaction in the Presence of Friedel-Crafts Catalysts
10(23)
Nucleoside Synthesis with SnCl and Related Friedel-Crafts Catalysts
10(5)
Nucleoside Formation with Trimethylsilyl Triflate
15(10)
Transglycosylation with Lewis Acids
25(4)
One Step-One Pot Nucleoside Syntheses
29(4)
Mechanism of Nucleoside Formation in the Presence of Friedel-Crafts Catalysts
33(16)
Experimental Results
33(5)
Reversible σ-Complex Formation between Silylated Bases and Friedel-Crafts Catalysts
38(6)
Mechanism of Pyrimidine and Purine Nucleoside Synthesis
44(2)
Regioselectivity of Nucleoside Formation
46(3)
Special Preparations
49(18)
Synthesis of 2'-Deoxynucleoxides
49(7)
Chemical Conversion of Ribo-to 2'-Deoxyribonucleosides
56(2)
Synthesis of β-D-Arabinofuranosylpyrimidine and Purine Nucleosides
58(9)
Miscellaneous Methods
67(9)
Alternative Silyl-Hilbert-Johnson Procedures
67(9)
Catalysis by Alkali Halides
67(1)
Activation of t-Sulfur Groups
68(4)
Alternative Formation of 1-Sugar Cations
72(3)
Variations of the Hilbert-Johnson Reaction
75(1)
Alternative Nucleoside-Forming Reactions
76(13)
Nucleoside Synthesis with Protected 1-Hydroxysugars
76(4)
Construction of the Heterocyclic Base to Unsaturated Systems
80(5)
Conjugate Addition of Heterocyclic Bases to Unsaturated Systems
85(1)
Enzymatic Transglycosylations
85(4)
Experimental Conditions
89(12)
Sugar Moieties
89(1)
Heterocycles
90(1)
Silylation
91(2)
Friedel-Crafts Catalysts
93(1)
Solvents
94(4)
Workup of Friedel-Crafts-Catalyzed Silyl-Hilbert-Johnson Reactions Removal of O-Acyl, N-Acyl, O-Benzyl, or O-Silyl Protecting Groups
98(2)
Melting Points of Free Nucleosides
100(1)
Experimental Procedures
101(5)
2',3',5'-Tri-O-benzoyl-5-nitrouridine
102(1)
1-β-D-Ribofuranosyl-2-pyridin-2-one
102(1)
5-Methoxyuridine-2',3',5'-tri-O-benzoate
103(1)
Guanosine
104(1)
1-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-and-β-D-glucopyranosyl)thymine
104(1)
2,6-Dichloro-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazo-[4,5-c]pyridine
105(1)
4-Methoxy-2-(methylthio)-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo-[2,3d]pyrimidine
105(1)
3',5'-Di-O-toluoytthymidine
106(1)
Tabular Survey
106(484)
Table I. One Step-One Pot Silylation/Coupling of Heterocyclic Bases with Sugars-Friedel-Crafts Catalysts
110(30)
Table II. One Step-One Pot Coupling of Heterocyclic Bases with Sugars-Friedel-Crafts Catalysts
140(12)
Table III. Reactions of Silylated Heterocyclic Bases with Protected Sugars-SnCl4 Catalyst
152(131)
Table IV. Analogous Reactions with Trimethylsilyl and Silver Triflates and Perchlorates
283(99)
Table V. Reactions with TiCl4 as Catalyst
382(7)
Table VI. Reactions with BF3 - OEt2 as Catalyst
389(11)
Table VII. Reactions with Miscellaneous Friedel-Crafts Catalysts
400(15)
Table VIII. Reactions of Silylated Bases with Protected Sugars with or without Catalysts
415(76)
Table IX. Fusion Reactions
491(25)
Table X. Miscellaneous Reactions of Heterocyclic Bases with Protected Sugars
516(34)
Table XI. Reactions of Acidic Heterocycles with 1-Halosugars in the Presence of Bases
550(40)
References 590(39)
Index 629

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