ORGANIC SYNTHESIS WITH CARBOHYDRATES,9781850759133

ORGANIC SYNTHESIS WITH CARBOHYDRATES

by ;
Edition: 1st
ISBN13: 9781850759133
ISBN10: 1850759138
Format: Hardcover
Pub. Date: 2000-02-21
Publisher(s): Wiley-Blackwell
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Summary

This book provides a broad understanding of the use of carbohydrates in organic synthesis. Emphasis is placed on retrosynthetic analysis, with discussion of why a particular synthetic route has been chosen, and mechanistic explanations are provided for key and novel reactions. Wherever possible, the authors highlight points of general significance to organic synthesis.The volume is intensively referenced and so provides a convenient point of entry to the research literature.

Author Biography

GEERT-JAN BOONS, PhD, is Franklin Professor of Chemistry and Professor in the Complex Carbohydrate Research Center at the University of Georgia. He is on the editorial boards of several journals on carbohydrates, including the European Journal of Chemistry and the Journal of Carbohydrate Chemistry, and is also coeditor of Carbohydrate-Based Immunotherapies and Vaccines.

KARL J. HALE obtained his Ph.D in Synthetic Carbohydrate Chemistry from King's College London in 1985. He is a professor in the School of Chemistry and Chemical Engineering at Queen's University in Belfast. Professor Hale has been the recipient of a number of prestigious learned society awards, fellowships, and named lectureships, including the 2012 Royal Society of Chemistry All Ireland Symposium Lectureship.

Table of Contents

PART A: STRUCTURE AND SYNTHESIS OF SACCHARIDES AND GLYCOPROTEINS
Mono- and oligosaccharides: structure, configuration and conformation
1(25)
Introduction
1(1)
Configuration of monosaccharides
2(5)
Conformational properties of monosaccharides
7(11)
Ring shapes of pyranoses and furanoses
7(3)
The anomeric effect
10(5)
The equilibrium composition of monosaccharides in solution
15(3)
Conformational properties of oligosaccharides
18(1)
Acid-catalysed glycoside bond formation and cleavage
19(7)
References
24(2)
Protecting groups
26(30)
Introduction
26(1)
Ether protecting groups
27(14)
Benzyl ethers
27(6)
p-Methoxybenzyl ethers
33(1)
Allyl ethers
34(3)
Triphenylmethyl ethers
37(1)
Silyl ethers
38(3)
Acetal protecting groups
41(5)
Benzylidene acetals
41(2)
Isopropylidene acetals
43(2)
Dispirodiketal and cyclohexane-1,2-diacetal groups
45(1)
Ester protecting groups
46(3)
Anomeric protecting groups
49(2)
Amino protecting groups
51(5)
Phthalimides
52(1)
Azides
52(1)
References
53(3)
Functionalised saccharides
56(47)
General introduction
56(1)
Deoxyhalogeno sugars
56(9)
Introduction
56(1)
Direct halogenation of alcohols
56(4)
Displacement reactions
60(3)
Miscellaneous methods
63(2)
Unsaturated sugar derivatives
65(6)
Introduction
65(1)
Glycals
66(3)
Isolated double bonds
69(1)
6-Deoxy-hex-5-enopyranose derivatives
69(2)
Deoxy sugars
71(5)
Introduction
71(1)
Reduction of halides, sulfonates and epoxides
72(2)
Radical deoxygenation of thiocarbonyl derivatives
74(2)
Amino sugars
76(8)
Introduction
76(1)
The preparation of amino sugars by nucleophilic displacement
77(4)
Addition to glycals
81(1)
Reduction of oximes
82(2)
Intramolecular substitutions
84(1)
Epoxy sugars
84(3)
Sulfated saccharides
87(2)
Introduction
87(2)
O and N sulfation
89(1)
Phosphorylated saccharides
89(14)
Introduction
89(1)
Non-anomeric sugar phosphates
90(4)
Anomeric phosphates
94(2)
References
96(7)
Oligosaccharide synthesis
103(52)
Introduction
103(1)
Chemical glycosidic bond synthesis
103(7)
Glycosyl halides
105(2)
Trichloroacetimidates
107(2)
Thioglycosides
109(1)
Stereoselective control in glycosidic bond synthesis
110(12)
Neighbouring-group-assisted procedures
111(1)
In situ anomerisation
112(2)
Glycosylation with inversion of configuration
114(4)
Solvent participation
118(2)
Intramolecular aglycon delivery
120(2)
Preparation of 2-amino-2-deoxy-glycosides
122(2)
Formation of glycosides of N-acetyl-neuraminic acid
124(3)
The introduction of 2-deoxy glycosidic linkages
127(4)
Convergent block synthesis of complex oligosaccharides
131(4)
Chemoselective glycosylations and one-pot multistep glycosylations
135(4)
Solid-phase oligosaccharide synthesis
139(5)
Enzymatic glycosylation strategies
144(11)
Glycosyl transferases
146(2)
Glycosyl hydrolases
148(2)
References
150(5)
The chemistry of O- and N-linked glycopeptides
155(20)
Introduction
155(1)
Strategies for the chemical synthesis of glycopeptides
156(4)
Protecting groups in glycopeptide synthesis
160(1)
Chemical synthesis of serine O-glycoside derivatives
161(5)
The synthesis of N-glycopeptides
166(1)
Solution-phase and solid-phase glycopeptide synthesis
167(4)
Enzyme-mediated glycopeptide synthesis
171(4)
References
172(3)
PART B: NATURAL PRODUCT SYNTHESIS FROM MONOSACCHARIDES
(-)-Echinosporin
175(11)
Introduction
175(1)
Smith's retrosynthetic analysis of (-)-echinosporin
175(1)
Smith's (-)-echinosporin synthesis
176(5)
Mechanistic analysis of some key reactions employed in the Smith (-)-echinosporin synthesis
181(5)
References
184(2)
(+)-Zaragozic acid C
186(14)
Introduction
186(1)
Carreira's retrosynthetic analysis of (+)-zaragozic acid C
186(2)
Carreira's total synthesis of (+)-zaragozic acid C
188(6)
Mechanistic analysis of some of the key steps in Carreira's synthesis of (+)-zaragozic acid C
194(6)
References
198(2)
(+)-Neocarzinostatin
200(17)
Introduction
200(1)
Myers' retrosynthetic planning for the synthesis of (+)-neocarzinostatin
200(6)
Myers' total synthesis of (+)-neocarzinostatin
206(5)
Mechanistic analysis of the key steps in Myers'(+)-neocarzinostatin synthesis
211(6)
References
215(2)
(+)-Castanospermine
217(7)
Introduction
217(1)
The Pandit retrosynthetic analysis of (+)-castanospermin
217(1)
Pandit's total synthesis of (+)-castanospermine
218(3)
Mechanistic analysis of the Pandit synthesis of (+)-castanospermine
221(3)
References
222(2)
(-)-Silphiperfolene
224(10)
Introduction
224(1)
The Fraser-Reid retrosynthetic analysis of (-)-silphiperfolene
224(5)
Fraser-Reid's total synthesis of (-)-silphiperfolene
229(3)
Mechanistic analysis of the Fraser-Reid (-)-silphiperfolene synthesis
232(2)
References
232(2)
(-)-Allosamizoline
234(13)
Introduction
234(1)
The Kuzuhara retrosynthetic analysis of (-)-allosamizoline
235(1)
The Kuzuhara total synthesis of (-)-allosamizoline
236(3)
Mechanistic analysis of the Kuzuhara (-)-allosamizoline synthesis
239(1)
Simpkins' retrosynthetic strategy for (-)-allosamizoline
239(2)
Simpkins' total synthesis of (-)-allosamizoline
241(2)
Mechanistic analysis of some key steps in the Simpkins (-)-allosamizoline synthesis
243(2)
Epilogue
245(2)
References
245(2)
(-)-Reiswigin A
247(12)
Introduction
247(1)
The Kim retrosynthetic analysis of (-)-reiswigin A
247(4)
The Kim total synthesis of (-)-reiswigin A
251(3)
Mechanistic points of interest in the (-)-reiswigin A synthesis
254(5)
References
257(2)
(-)-Octalactin A
259(11)
Introduction
259(1)
The Buszek retrosynthetic analysis of (-)-octalactin A
259(5)
Buszek's total synthesis of (-)octalactin A
264(1)
Items of mechanistic interest in the Buszek (-)-octalactin A synthesis
265(5)
References
269(1)
(-)-ACRL toxin I
270(10)
Introduction
270(1)
The Lichtenhaler retrosynthetic analysis of (-)-ACRL toxin I
270(3)
Lichtenhaler's total synthesis of the (-)-ACRL toxin I
273(4)
Items of mechanistic interest in the Lichtenhaler synthesis of the (-)-ACRL toxin I
277(2)
Epilogue
279(1)
References
279(1)
(+)-Gabosine E
280(6)
Introduction
280(1)
The Lygo retrosynthetic analysis of (+)-gabosine E
280(2)
The Lygo synthesis of (+)-gabosine E
282(2)
Points of mechanistic interest in the Lygo (+)-gabosine E synthesis
284(2)
References
285(1)
(-)-Augustamine and (-)-amabiline
286(6)
Introduction
286(1)
The Pearson retrosynthetic analysis of (-)-augustamine
286(2)
The Pearson total synthesis of (-)-augustamine
288(2)
Pearson's synthesis of (-)-amabiline
290(1)
Mechanistic analysis of the (-)-augustamine and (-)-amabiline syntheses
290(2)
References
291(1)
(-)-FK506
292(37)
Introduction
292(1)
The Danishefsky retrosynthetic analysis of (-)-FK506
292(3)
The Danishefsky formal total synthesis of (-)-FK506
295(7)
The Merck endgame used in the first total synthesis of (-)-FK506
302(3)
Smith's retrosynthetic analysis of (-)-FK506
305(3)
The Smith formal total synthesis of (-)-FK506
308(9)
Items of interest in the Danishefsky and Smith total syntheses of (-)-FK506
317(12)
References
326(3)
(3S,5S)-5-Hydroxypiperazic acid
329(5)
Introduction
329(1)
The Hale retrosynthetic analysis of (3S,5S)-5-hydroxypiperazic acid
329(2)
The Hale total synthesis of (3S,5S)-5-hydroxypiperazic acid
331(1)
Points of mechanistic interest in the Hale (3S,5S)-5-hydroxypiperazic acid synthesis
332(2)
References
333(1)
Index 334

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