C-glycoside synthesis:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Boca Raton u.a.
CRC Press
1995
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | 379 S. graph. Darst. |
| ISBN: | 0849391504 |
Internformat
MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV010493431 | ||
| 003 | DE-604 | ||
| 005 | 00000000000000.0 | ||
| 007 | t | ||
| 008 | 951124s1995 d||| |||| 00||| engod | ||
| 020 | |a 0849391504 |9 0-8493-9150-4 | ||
| 035 | |a (OCoLC)31411580 | ||
| 035 | |a (DE-599)BVBBV010493431 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-355 | ||
| 050 | 0 | |a QP702.G59 | |
| 082 | 0 | |a 547.7/83 |2 20 | |
| 084 | |a VK 8600 |0 (DE-625)147543:253 |2 rvk | ||
| 100 | 1 | |a Postema, Maarten H. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a C-glycoside synthesis |c Maarten H. D. Postema |
| 264 | 1 | |a Boca Raton u.a. |b CRC Press |c 1995 | |
| 300 | |a 379 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 7 | |a Hétérosides - Synthèse |2 ram | |
| 650 | 4 | |a Glycosides |x Synthesis | |
| 650 | 4 | |a Glycosides |x chemical synthesis | |
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Glykoside |0 (DE-588)4021359-6 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Glykoside |0 (DE-588)4021359-6 |D s |
| 689 | 0 | 1 | |a Chemische Synthese |0 (DE-588)4133806-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 856 | 4 | 2 | |m HEBIS Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006992312&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-006992312 | ||
Datensatz im Suchindex
| _version_ | 1804124926606573568 |
|---|---|
| adam_text | Table of Contents
Chapter 1 Electrophilic Sugars in C-Glycoside Synthesis I 1
I INTRODUCTION 1
II LACTOLS 1
A Silicon and Aromatic Based Nucleophiles 1
1 Enol Ethers 1
2 Aromatic Nucleophiles 2
a Rearrangement 2
b Phenolates 4
3 Stabilized Nucleophiles 5
B Organometallic Nucleophiles 5
III O-GLYCOSIDES 6
A Silicon Based Nucleophiles 6
1 Allylsilanes 6
2 Aromatic Nucleophiles 10
3 Stabilized Nucleophiles 10
IV S-GLYCOSIDES 11
A Thiopyridyl Glycosides 11
1 Intermolecular Condensations 11
2 Intramolecular Condensations 11
B Phenyl Thioglycosides 12
C Anomeric Sulfones 14
1 With Enol Ethers 14
V ANOMERIC O-TRICHLOROACETIMIDATES 15
A Silyl Enol Ethers 15
B Aromatics 16
VI ANOMERIC ACETATES 17
A Silicon Based Nucleophiles 17
1 Pyranosides 17
2 Furanosides 21
B Aromatic Nucleophiles 24
C Organometallics 27
VII GLYCOSYL HALIDES 28
A Glycosyl Chlorides 28
1 Silicon Based Nucleophiles and Aromatics 28
2 Organometallic Reagents 30
3 Stabilized Nucleophiles 31
B Glycosyl Bromides 31
1 Amino C-Glycosides 31
2 Aromatics 33
3 Organometallics 33
C Glycosyl Fluorides 37
1 Silicon Based Nucleophiles 37
2 Aromatics 38
3 Aluminum Based Reagents 39
VIII REFERENCES 40
Chapter 2 Electrophilic Sugars in C-Glycoside Synthesis II 43
I INTRODUCTION 43
II GLYCALS 43
A Enol Ethers and Related Species 43
B Allylation 45
C Olefins 49
D Aromatics 51
E Cyanides 53
F Organometallics 54
III ENITOLS AND ANHYDRO SUGARS 55
A Enitols 55
1 Addition of Cyanide and Enol Ethers 55
2 Cuprates 56
3 Aromatics 56
B Anhydro Sugars 56
IV LACTONES 57
V INTRAMOLECULAR ARYLATION 60
VI CONCLUSION 63
VII REFERENCES 63
Chapter 3 C-l Nucleophiles in C-Glycoside Preparation 65
I INTRODUCTION 65
II C-l STABILIZED ANIONS 65
A Anomeric Nitrosugars 65
B Anomeric Esters 67
C Stabilization by Phosphorous 69
D Use of Sulfur 70
III ANOMERIC ANIONS 72
A Reductive Metallation 72 ’
1 Sulfides 72
2 Sulfones 74
3 Anomeric Lithio Derivatives 76
b From Chlorides 76
c Anomeric Stannanes 76
4 Anomeric Copper Derivatives 78
5 Anomeric Organosamarium Derivatives 80
IV TRANSITION METAL ANOMERIC COMPLEXES 81
A Anomeric Manganese Complexes 81
B Anomeric Cobalt Complexes 83
V C-l VINYL ANIONS 83-
A Non-Stabilized C-l Anions 83
1 From Glycals 83
B C-2 Stabilized C-1 Anions 87
VI CONCLUSION 88
VII REFERENCES 89
Chapter 4 Wittig Approaches to C-Glycoside Formation 91
I INTRODUCTION 91
II USE OF STABILIZED PHOSPHORANES 91
A C-Furanosides 91
B C-Pyranosides 95
III HORNER-EMMONS-WADSWORTH-APPROACHES 101
IV OLEFINATION FOLLOWED BY ELECTROPHILIC CYCLIZATION 103
A Mercuriocyclization 103
B Halocyclization 105
C Selenocyclization 109
V USE OF SULFUR YLIDES 110
VI OLEFINATION OF SUGAR LACTONES 112
VII CONCLUSION 116
VIII REFERENCES 116
Chapter 5 Palladium Mediated Approaches to C-Glycosides 119
I INTRODUCTION 119
II 7i-ALLYL COMPLEXES 119
III HECK TYPE COUPLINGS 126
A Use of Glycals 127
B Use of Anomeric Stannanes 134
IV CONCLUSION 137
V REFERENCES 138
Chapter 6 Concerted Reactions Applied to C-Glycoside Preparation 139
I INTRODUCTION 139
II SIGMATROPIC REARRANGEMENTS 139
A Claisen Rearrangement 139
B Ireland-Claisen Rearrangement 140
C Wittig Rearrangement 147
III CYCLOADDITIONS 148
A Formation of the Pyran Ring 149
B Formation of the C-Glycoside Bond 154
1 [4+2] Cycloaddition 154
2 [2+2] Photocycloaddition 155
C Cycloaddition Reactions of C-Glycosides 156
IV CONCLUSION 159
V REFERENCES 160
Chapter 7 Free Radical Approaches to C-Glycosides 161
I INTRODUCTION 161
II INTERMOLECULAR ADDITIONS 163
A Michael Acceptors 163
B Radical Addition to Exomethylenic Sugars 171
C Keck Allylation 172
D Reduction to ß-C-Pyranosides 175
III INTRAMOLECULAR APPROACHES 179
IV ANOMERIC CARBENES 190
V CONCLUSION 191
VI REFERENCES 191
Chapter 8 C-Disaccharide Synthesis 193
I INTRODUCTION 193
II SYNTHETIC APPROACHES TO C-DISACCHARIDES 194
A Anionic Approaches 194
1 Carbanionic Methods 194
2 Use of Nitrosugars 202
B Free Radical Approaches 205
1 Intermolecular Additions 205
2 Intramolecular Approaches 212
C Cycloaddition Approaches 214
D Cationic Approaches 216
E Wittig Approaches 219
III SYNTHETIC APPROACHES TO C-TRISACCHARIDES 223
A Aldol Approach to a C-Trisaccharide 223
IV CONCLUSION 225
V REFERENCES 226
Chapter 9 Synthesis of Alkyl C-Glycoside Natural Products 227
I INTRODUCTION 227
II ALKYL C-PYRANOSIDE NATURAL PRODUCTS 228
A Ambruticin 228
1 Isolation and Structure Determination 228
2 Total Synthesis of Ambruticin 228
B Pseudomonic Acids 233
1 Isolation and Structure 233
2 Synthesis of Pseudomonic Acids 234
III ALKYL C-FURANOSIDE NATURAL PRODUCTS 253
A Muscarines 253
1 Isolation 253
2 Syntheis of Muscarines 254
a From Carbohydrates 254
b Cyclofunctionalization Approaches 256
c Direct Cyclization 258
d Ring Expansion 260
IV CONCLUSION 261
V REFERENCES 262
Chapter 10 Synthesis of Naturally Occurring Aryl C-Glycosides 265
I INTRODUCTION 265
II ARYL C-GLYCOSIDE NATURAL PRODUCTS 265
A Nogalamycin and its Congeners 265
1 Structure and Properties 265
2 Synthesis of the Nogalamycins 266
B Chaetiacandin and the Papulacandins 277
1 Structure and Properties 277
2 Synthesis of Papulacandins 278
C Vineomycin-Fridamycin Antibiotics and Related Compounds 283
1 Structure and Properties 283
2 Synthesis of Vineomycinone B2 Methyl Ester 284
3 Medermycin 289
D Gilvocarcin Antibiotics 290
1 Introduction 290
2 Synthetic Work 291
E Miscellaneous Aryl C-Glycosides 294
1 (-)-Urdamycinone B 294
2 Carminic Acid 295
3 Bergenin 296
4 C-Glycosyl Flavanoids 297
a 5,7,4 -Tri-0-Methylvitexin 297
b Bayin Flavanoids
III CONCLUSION
IV REFERENCES
Chapter 11 C-Nucleoside Synthesis
I SOME BIOLOGICALLY RELEVANT C-NUCLEOSIDES
II SYNTHETIC APPROACHES TO C-NUCLEOSIDES
A Free Radical Approaches
1 Mutiple Bond Addition
a Addition to a Base Precursor
b Addition to a Heterocycle
B Wittig Approaches
1 Attachment of a Carbon Fragment
2 Attachment of the Heterocycle
C Friedel-Crafts Approaches
1 Glycosidation with a Heterocycle
2 Glycosidation with a Carbon Fragment
Followed by Heterocycle Formation
D One Carbon Introduction in C-Nucleoside Synthesis
1 Esters, Nitriles, and Acids
2 Aldehydes and Other Groups
E Nucleophilic Addition
1 Lithiated Heterocycles
2 Carbon Based Nucleophiles
F The Bicyclo Approach
G Cyclization of Alditols
III CONCLUSION
IV REFERENCES
Chapter 12 Biological and Practical Applications of C-Glycosides
I INTRODUCTION
II BIOLOGICAL APPLICATIONS
A Enzyme Inhibitors
B Labeling
C Anti-Viral and Anti-Microbial Agents
D Anti-Cancer Activity
E C-Disaccharides
F C-Phosphonate Analogs
III OTHER APPLICATIONS
IV CONCLUSION
V REFERENCES
298
300
301
303
303
305
306
306
306
306
308
308
312
315
315
316
319
319
324
328
328
332
334
339
341
342
345
345
345
346
354
355
360
362
362
363
365
365
Index
|
| any_adam_object | 1 |
| author | Postema, Maarten H. |
| author_facet | Postema, Maarten H. |
| author_role | aut |
| author_sort | Postema, Maarten H. |
| author_variant | m h p mh mhp |
| building | Verbundindex |
| bvnumber | BV010493431 |
| callnumber-first | Q - Science |
| callnumber-label | QP702 |
| callnumber-raw | QP702.G59 |
| callnumber-search | QP702.G59 |
| callnumber-sort | QP 3702 G59 |
| callnumber-subject | QP - Physiology |
| classification_rvk | VK 8600 |
| ctrlnum | (OCoLC)31411580 (DE-599)BVBBV010493431 |
| dewey-full | 547.7/83 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.7/83 |
| dewey-search | 547.7/83 |
| dewey-sort | 3547.7 283 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01441nam a2200397 c 4500</leader><controlfield tag="001">BV010493431</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">00000000000000.0</controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">951124s1995 d||| |||| 00||| engod</controlfield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">0849391504</subfield><subfield code="9">0-8493-9150-4</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)31411580</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)BVBBV010493431</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakddb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-355</subfield></datafield><datafield tag="050" ind1=" " ind2="0"><subfield code="a">QP702.G59</subfield></datafield><datafield tag="082" ind1="0" ind2=" "><subfield code="a">547.7/83</subfield><subfield code="2">20</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 8600</subfield><subfield code="0">(DE-625)147543:253</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Postema, Maarten H.</subfield><subfield code="e">Verfasser</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">C-glycoside synthesis</subfield><subfield code="c">Maarten H. D. Postema</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">Boca Raton u.a.</subfield><subfield code="b">CRC Press</subfield><subfield code="c">1995</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">379 S.</subfield><subfield code="b">graph. Darst.</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Hétérosides - Synthèse</subfield><subfield code="2">ram</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Glycosides</subfield><subfield code="x">Synthesis</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Glycosides</subfield><subfield code="x">chemical synthesis</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Chemische Synthese</subfield><subfield code="0">(DE-588)4133806-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Glykoside</subfield><subfield code="0">(DE-588)4021359-6</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Glykoside</subfield><subfield code="0">(DE-588)4021359-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2="1"><subfield code="a">Chemische Synthese</subfield><subfield code="0">(DE-588)4133806-6</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">HEBIS Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006992312&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-006992312</subfield></datafield></record></collection> |
| id | DE-604.BV010493431 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T17:53:26Z |
| institution | BVB |
| isbn | 0849391504 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-006992312 |
| oclc_num | 31411580 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR |
| owner_facet | DE-355 DE-BY-UBR |
| physical | 379 S. graph. Darst. |
| publishDate | 1995 |
| publishDateSearch | 1995 |
| publishDateSort | 1995 |
| publisher | CRC Press |
| record_format | marc |
| spelling | Postema, Maarten H. Verfasser aut C-glycoside synthesis Maarten H. D. Postema Boca Raton u.a. CRC Press 1995 379 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Hétérosides - Synthèse ram Glycosides Synthesis Glycosides chemical synthesis Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Glykoside (DE-588)4021359-6 gnd rswk-swf Glykoside (DE-588)4021359-6 s Chemische Synthese (DE-588)4133806-6 s DE-604 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006992312&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Postema, Maarten H. C-glycoside synthesis Hétérosides - Synthèse ram Glycosides Synthesis Glycosides chemical synthesis Chemische Synthese (DE-588)4133806-6 gnd Glykoside (DE-588)4021359-6 gnd |
| subject_GND | (DE-588)4133806-6 (DE-588)4021359-6 |
| title | C-glycoside synthesis |
| title_auth | C-glycoside synthesis |
| title_exact_search | C-glycoside synthesis |
| title_full | C-glycoside synthesis Maarten H. D. Postema |
| title_fullStr | C-glycoside synthesis Maarten H. D. Postema |
| title_full_unstemmed | C-glycoside synthesis Maarten H. D. Postema |
| title_short | C-glycoside synthesis |
| title_sort | c glycoside synthesis |
| topic | Hétérosides - Synthèse ram Glycosides Synthesis Glycosides chemical synthesis Chemische Synthese (DE-588)4133806-6 gnd Glykoside (DE-588)4021359-6 gnd |
| topic_facet | Hétérosides - Synthèse Glycosides Synthesis Glycosides chemical synthesis Chemische Synthese Glykoside |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006992312&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT postemamaartenh cglycosidesynthesis |