I= SYNTHESES OF AMINO AND CYANODEOXY SUGARS VIA EPOXY SUGAR INTERMEDIATES AND PHYTOCHEMICAL STUDIES OF SAPONARIA VACCARIA AND PLUMERIA RUBRA
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Title of Thesis
SYNTHESES OF AMINO AND CYANODEOXY SUGARS VIA EPOXY SUGAR INTERMEDIATES AND PHYTOCHEMICAL STUDIES OF SAPONARIA VACCARIA AND PLUMERIA RUBRA

Author(s)
Syed Najam-ul-Hassan Kazmi
Institute/University/Department Details
University of Karachi/ H.E.J. Research Institute of Chemistry
Session
1990
Subject
Chemistry
Number of Pages
282
Keywords (Extracted from title, table of contents and abstract of thesis)
cyanodeoxy sugars, epoxy sugar, saponaria vaccaria, plumeria rubra, aminodeoxy sugars, oxirane, monosaccharide amino sugars, phytoxanthone, saponaria

Abstract
This thesis presents the work in three parts. The Part-A describes the syntheses of aminodeoxy sugars (8-15) and cyanodeoxy sugars (16-20) via 2,3-anhydro sugars (1-7).

In the reaction sequence region selective trans-diaxial cleavage of oxirane ring in 2,3-anhdro sugars have been affected with trimethyl silyl diethylamine, trimethyl silyl dimethylamine, and trimethyl silyl cyanide. The following new compounds have been obtained…...

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S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents/ Summary
297.11 KB
2 1 Part-A: Introduction 23
373.2 KB
  1.1 Biological Importance 24
  1.2 Naturally Occurring Monosaccharide Amino Sugars 29
  1.3 Synthesis Of Monosaccharide Amino Sugars 47
3 2 Results And Discussion Syntheses Of Sugar Epoxides 78
91.34 KB
  2.1 Synthesis Of Methyl 2 ,3 -Anhydro-4-6-O-Benzylidene –A-D- Allopyranoside (1) 78
  2.2 Synthesis Of Methyl 2 ,3 -Anhydro-4-6-O-Benzylidene –A-D- Allopyranoside (2) 80
  2.3 Sunthesis Of Benzyl 2 ,3 -Anhdro-B-L-Ribopyranoside (3) 82
  2.4 Sunthesis Of Benzyl 2 ,3 -Anhdro-D-L-Ribopyranoside (4) 84
  2.5 Sunthesis Of Benzyl 2 ,3 -Anhdro-D-L-Ribopyranoside (5) 87
  2.6 Synthesis Of Methyl 2 ,3 -Anhydro-6-Deoxy-A-D-Allopyranoside(6) 89
  2.7 Synthesis Of Methyl 2 ,3 -Anhydro-A-D-Allopyranoside (7) 91
4 3 Aminodeoxy Sugars 92
85.07 KB
  3.1 Syntheses Of Aminodeoxy Sugars (8-15) 92
  3.2 Field Desorption Mass And Infrared Spectrometry Of Aminodeoxy Sugars 98
  3.3 H-Nmr Spectral Studies Of Aminodeoxy Sugars 99
  3.4 13c-Nmr Spectral Studies Of Aminodeoxy Sugars 102
5 4 Cyanodeoxy Sugars 104
100.92 KB
  4.1 Syntheses Of Cyanodeoxy Sugars (16-20) 104
  4.2 Field Desorption Mass And Infrared Spectrometry Of Cyanodeoxy Sugars 98
  4.3 H-Nmr Spectral Studies Of Cyanodeoxy Sugars 99
  4.4 13c-Nmr Spectral Studies Of Cyanodeoxy Sugars 102
  4.5 Conversion Of Cyanodeoxy Sugars Into Aminomethyl Sugars (21-25) 114
  4.6 Conversion Of Cyanodeoxy Sugars Into Sugar Amides (26-30) 116
6 5 Experimental 118
190.28 KB
  5.1 Chemicals 118
  5.2 Solvents 118
  5.3 Chromatographic Methods 118
  5.4 Color Reagents 119
  5.5 Spectroscopic Methods 120
  5.6 Physical Methods 121
  5.7 Syntheses Of Sugar Epoxides (1-7) 122
  5.8 Methyl 2 ,3 -Anhydro-4,6-O-Benzylidene-A-D-Allopyranoside(1) 122
  5.9 Methyl 2 ,3 -Anhydro-4,6-O-Benzylidene-A-D-Allopyranoside(2) 126
  5.10 Benzyl 2,3-Anhydro-B-L-Ribopyranoside(3) 128
  5.11 Benzyl 2 ,3 -Anhydro-A-L-Ribopyranoside(4) 132
  5.12 Benzyl 2 ,3 -Anhydro-A-L-Ribopyranoside(5) 138
  5.13 Methyl 2 ,3 -Anhydro-6-Deoxy-A-D-Allopyranoside (6) 141
  5.14 Methyl 2 ,3 -Anhydro-A-D-Allopyranoside (7) 121
7 6 Syntheses Of Aminodeoxy Sugars (8-15) 147
322.64 KB
  6.1 Syntheses Of Cyanodeoxy Sugars (16-20) 154
  6.2 Syntheses Of Aminomethyl Deoxy Sugars (21-25) 159
  6.3 Syntheses Of Amino Deoxy Sugars (26-30) 164
  6.4 References 168
8 7 Part-B: Introduction 194
168.13 KB
  7.1 Classification Of Phytoxanthone 194
  7.2 Therapeutic Utility Of Phytoxanthone 198
  7.3 Chemotaxonomic Aspects 202
  7.4 Phytochemistry Of Genus Saponaria 205
  7.5 Literature Survey Of Saponaria Vaccaria 218
9 8 Results And Discussion 220
126.81 KB
  8.1 New Compounds From Saponaria Vaccaria 220
  8.2 Vaccaxathone (24) 222
  8.3 Sapxanthone (25) 226
  8.4 Vaccariose (26) 230
  8.5 Unreported Xanthone From Saponaria Vaccaria Swerchirin (Methyl Bellidifolium ) (27) 233
10 9 Experimental 236
126.41 KB
  9.1 General Notes 236
  9.2 Plant Material Extraction And Purification 237
  9.3 Vaccaxanthone (24) 238
  9.4 Sapxanthone (25) 241
  9.5 Vaccariose (26) 244
  9.6 Swerchirin (Methyl Bellidifolium ) (27) 247
  9.7 Vaccarin (19) 249
  9.8 Vaccaegoside B (20) 250
  9.9 Vaccaegoside C (21) 251
11 10 References 252
82.13 KB
12 11 Part-C-Introduction 262
39.62 KB
13 12 Results And Discussion 267
14.29 KB
14 13 Experimental 275
122.07 KB
15 14 References 279
47.69 KB