A B C D

INDEX

Downloaded by 223.104.6.2 on June 7, 2018 | https://pubs.acs.org Publication Date: June 1, 1968 | doi: 10.1021/ba-1968-0074.ix001

A Abequose Acetic anhydride Acetone-d6 /J-Acetyl acrolein in Dische test . . . Acetylated sugars, mass spectra of . Acetylating agent Acetylformamide Acid anhydride-methyl sulfoxide . . 0 - Acyldeoxyglycosyl halides Aldosuloses, deoxy sugars from . . . . Alkoxysulfonium salts Alkyl halides, reaction of sugar phosphorodiamide and phosphonamide derivatives with 3-Amino-3-deoxy-D-glucose Angular dependence of vicinal coupling constants Angustmycin A Anomalies of unsaturated sugar derivatives Anomers of 2-deoxy-D-arafcinohexopyranose Antiaris toxicaria Lesch Ascelepias lilacina Weimarck Ascelepias swynnertonii S. Moore 1- Ascorbic acids, periodate oxidation of

Chlorine at C - 6 with sulfuryl chloride, selective 107 introduction of 59 Chlorodeoxy sugars by reaction 209 with sulfuryl chloride 96 Chlorodeoxy sugars by thermal 206 decomposition of O-imino 196 ester chlorides, synthesis of . . . 28 N- (2-Chloro-l,l,2-trifluoroethyl) 56 diethylamine 1,11 Chromium peroxide-pyridine 141 complex, oxidation of 259 deoxyglycosides with the Configurational dependence Conformational inversion, rapid 178 chair-chair 183 Cordycepine Coupling constants, geminal 236 Cyclic phosphates of deoxy sugars . 120 Cyclitols 44, Cyclohexanepentols 41, 151 Cyclohexanes, hydroxylated 1-Cyclohexylamino 1-deoxy D233 fructose 4, 6-phosphate 61 Cytosinine 61 .. 61

B

C ....

176, 192,

179 192 192 143 237 244 77 247 74 110 106 41 91 120

D

100

Benzoic anhydride 60 4- 0-Benzoyl-6-bromo-6-deoxy-a-Dglucopyranoside 183 O-Benzylidene acetals, preperation of bromodeoxy sugars from . . . 183 Biosynthesis of kasugamycin 30 Bloch-Siegert shift 232 Bond charge 216 Boron trichloride 191 Bromodeoxy sugars from O-benzylidene acetals, preparation of . . 183

Carbohydrate phenylboronates 1,2-cis-Cardenolides Chair-chair conformational inversion, rapid Chalcose Chlorinated sugars by tosyl chloride Chlorinating agent

181

64 11 244 207 164 196

Decoyinine 120 2- Deoxycardenolide 3 Deoxycyclitols 41 3- Deoxy-1,2:5,6-di-O-isopropylideneD-xylo hexofuranose 208 6-Deoxy-6-fluoro-D-glucose 162 5- Deoxy-3-C-formyl-L-lyxose 122 2-Deoxy-D-galactose 6 6- Deoxy-a-D-glucopyranoside, methyl 126 6-Deoxy-/?-D-glucopyranose tetraacetate 138 2- Deoxy-D-and L-gZt/cero-tetrose-4phosphate 77 Deoxyglycosides, direct synthesis of 1 3- Deoxy n-g/wco-heptonic acid 7phosphate 86 3-Deoxy D-arafotno-heptulosonic acid 7-phosphate 8© 6-Deoxyhex-5-enose derivatives . . . . 120 2-Deoxy-D-arafcino-hexopyranose, anomers of 233 2-Deoxy L-arabino-hexose 6phosphate 70

Hanessian; Deoxy Sugars Advances in Chemistry; American Chemical Society: Washington, DC, 1968.


256

DEOXY

SUGARS

O-isopropylidene ketals of 202 , structure elucidation of 206 6-Deoxy-6-sulfo-4-glucose 125 145 56 6-Deoxy-L-talose 167 6 Desosamine, synthesis of Deuterium oxide 209 19 71 2V,AT-Diacetylkasugamine 8 Dialkyl dithioacetals, mass spectra of 206 71 2,4-Diamino-N - (carboxyformidoyl) 2,3,4,6-tetradeoxy-a-i>ara&ino72 hexopyranoside 30 97 58 165 Dicyclohexylcarbodiimide Dicyclohexylcarbodiimide-methyl sulfoxide-pyridinium phosphate 56 125 2,6-Dideoxy-3,4-di-0-p-nitrobenzoylD-nfro-hexosyl bromide 2 86 5,6-Dideoxy-5,6-epithio-l,2-0isopropylidene-/?-L-idofuranose. 245 86 42 4,6-Dideoxyhexosides, methyl 4,6-dichloro183 47 5,6-Dideoxy-l,2-0-isopropylidenea-D-xt/Zo-hex-5-enofuranose . . . 246 51 2,6-Dideoxy-D-nfro-hexose 1 107 208 3,6-Dideoxy-D-xt/Zo-hexose Diethyl dithioacetal derivatives, mass spectra of 205 D-erythro-pent-4enofuranoside, methyl . . . . 129, 138 Digitalis spp 1 5- Deoxy-l,2-0-isopropylidene-/?-LDigitoxose 1 fforeo-pent-D- enofuranose .126, 136 Dihydroxyfumaric acids, periodate 6- Deoxy-a-L-idopyranose oxidation of 100 1,2:5,6-Di-O-isopropylidene-atetraacetate 138 6-Deoxy-l ,2-O-isopropylidene-Dglucofuranose 60 1,2:5,6-Di-O-isopropylidene-Dglucofurnose 207 glucofuranose 192 6-Deoxy-2,3-0-isopropylidene-/?-D1,2:5,6-Di-O-isopropylidene-a-Df7ireo-hexulo-5-enofuranose 130, 138 nfrohexofuranos-3-ulose . . . . 57, 60 6-Deoxy-2,3-0-isopropylidene-/?-Darabino-hexulo furanose . .131, 138Dioxane derivatives 246 6-Deoxy kanamycin 172 Direct synthesis of dexyglycosides . . 1 1- (5-Deoxy-a-L-lyxofuranosyl) Dische test, f3-acetyl acrolein in . . . 96 uracil 133 E 6-Deoxy-2-0-methyl-4-allose, 237 syntheses of 56 Electronegativity 204 6-Deoxy-3-0-methyl-4-allose 61 Electron impact Ene-diols, reduction of iodates by . . 100 syntheses of 56 Deoxynucleosides 3 Esterification of 6-deoxy-2hydroxy-glycals 155 2- Deoxy-a-D-en/fhro-pentofuranosyl phosphate 79 Ethyl 4-0-methylsulfonyl-2,3,62-Deoxy-D-ert/f/iro-pentose 95 trideoxy-a-D-ert/f/iro-hexoside . . 170 5-phosphate 73 Eucalyptus populnea 44 2-Deoxy-D-fTireo-pentose Evatromonoside 3 5-phosphate 76 F 2- Deoxy pentoses, Webb and 230 Levy test 96 Field-sweep NMDR Formylating agent 192 3- Deoxy-D-ert/f/iro-pentose 216 5-phosphate 77 Fragment ions Frequency-sweep NMDR 231 3-Deoxy-L-£7ira?-pentose 78 5-phosphate 77 L-Fuculose 5-Deoxypent-4-enose derivatives . . . 120 Furanoid ring, ring expansion of a. . 146 Deoxy sugar phosphates 109 G Deoxy sugars D-Galactose, 2-deoxy6 from aldosuloses and glycopyranosiduloses 141 Galactose structure, introduction of halogen atoms at C-6 in the . . 186 glycosides of 202 122 from 2-hydroxyglycal esters 150 GDP-/?-L-fucose

4-Deoxy - ft-L-arabinohexopyranoside, methyl 6-Deoxyhexopyranoside phenylboronates, syntheses of . 2-Deoxy-/?-D-Zt/xo-hexose 2-Deoxy-D-Zt/xo-hexose, phosphate esters of 2-Deoxy-D-nfco-hexose 3-Deoxy-D-nfco-hexose 6-phosphate. 3-Deoxy-r>xt/Zo-hexose 6-phosphate. 3-Deoxy hexoses 4- Deoxy-r>xt/Zo-hexoses 4- Deoxy-a-D-zt/to-hexopyranoside, methyl 3-Deoxy-D-ert/f/iro-hexulosonic acid 6-phosphate 3-Deoxy-D-£/ireo-hexulosonic acid 6-phosphate Deoxyinosamines Deoxy inositols, NMR of Deoxy inositols, periodate titrations of 5-Deoxy-l ,2-O-isopropylidene-Dxt/Zo-hexofuranose 5-Deoxy-2,3-0-isopropylidene-/?-

125

4


257

INDEX

Geminal coupling constants Glucometasaccharinic acid 6-phosphate D-Glycero-tetrose-4-phosphate, 2-deoxy L-Glycero-tetrose-4-phosphate, 2-deoxyGlycopyranosiduloses, deoxy sugars from Glycoside phenylboronates Glycosides of deoxy sugars

247 82 77 77 141 64 202


H Halodeoxy sugars by displacement of sulfonate ester, preparation of using phosphorus-containing reagents, preparation of synthesis of a-Halo esters Halogenated carbohydrates Heptulosonic acid 7-phosphate,

K Kanamycin, 6-deoxy Kanosamine Karplus Kasugamine Kasugamycin Kasuganobiosamine Ketals of deoxy sugars, O-isopropylidene

172 183 237 19 15 19 202

L

Long-range coupling constants . . . . 240

M MacDonald-Fisher degradation 205 94 172 Malapradian reactions 97 159 Malonaldehyde adduct, 2-thiobarbituric acid- . . . 98 178 over-oxidation reaction of 98 198 Mass spectra of acetylated sugars 206 3- deoxy-D-arabino86 of dialkyl dithioacetals 206 Heptonic acid 7-phosphate, of diethyl dithioacetals 205 3-deoxy-D-gZuco86 of O-isopropylidene derivatives . . 205 Hexose, 3, 6-di-deoxy-D-xt/Zo 107 of methylated methyl glycosides . 206 Hexose 6-phosphate, 2-deoxy-Dof nucleosides 205 arabino 70 202 Hexose 6-phosphate, 3-deoxy-D-rifro 71 Mass spectrometry Hexose 6-phosphate, 3-deoxy-D-xt/Zo- 72 Mechanism of bromination by NBS. 185 Mercaptalation synthesis of deoxy Hexose, phosphate esters of sugars 145 2- deoxy-D-Zt/xo 71 100 Hexoses, pseudo 51 Mesoxalic dialdehyde Metastable ion 204 Hexose sulfonates, reactivity at C-4 in 168 Methanesulfonyl chloride in N,N-dimethyl-formamide 198 Hexos-5-uloses 123 Methyl 2,3-anhydro-4,6-0Hexulosonic acid 6-phosphate, benzylidene-a-D-allyopyranoside 196 3- deoxy-D-erythro86 Hidden resonance 232 Methylated methyl glycosides, mass spectra of 206 Hydrazines oxidized by alkyl iodides by iodine 191 Methyl 4,6-0-benzylidene-3-deoxy3 -phenylazoaldohexoHydrazino compound synthesis of pyranosides 61 deoxy sugars 145 Hydroboration 123 Methyl 6-chloro-6-deoxy-a-i>glucopy ranoside 197 2-Hydroxyglycal esters, doexy sugars from 150 Methyl 5-deoxy-D-xt/Zo-furanoside . . 207 Methyl 6-deoxy-a-D-glucopyranoside 126 Hydroxylated cyclohexanes 41 Hygromycin A 124 Methyl 4-deoxy-a-D-xt/Zohexopyranoside 125 I Methyl 4-deoxy-/?-L-arafcwohexopyranoside 125 Inositol 46 myo49 Methyl 2-deoxy /3-u-arabinohexopyranoside 4,6Iodates by ene-diols, reduction of . . 100 (phenyl phosphate) 74 Isomerization of tetra-O-acetyl-2hydroxy-D-glucal 151 Methyl 5-deoxy-2,3-0isopropylidene-jS-D-ert/t/iroIsomerization of tri-O esters of 2pent-4-enofuranside 129 hydroxy-D-xylal 155 Methyl 5-deoxy-2,3-0O-Isopropylidene derivatives, mass isopropylidene-/?-D-en/#irospectra of 205 pent-4-enofuranoside 138 O-Isopropylidene ketals of deoxy sugars 202, 207 Methyl 2-deoxy-5-0-methyl-/?-Den/f/iro-pentofuranoside 207 Methyl 3-deoxy-5-0-methyl-/?J en/tfiro-pentofuranoside 207 D-Javose 61 160



258

D E O X Y SUGARS

Methyl 3-deoxy-/?-D-£/ireopentopyranoside Methyl 4-deoxy-ft-n-threopentopyranoside Methyl 4,6-dichloro-4,6dideoxyhexosides Methyl glycosides of deoxy sugars . Methyl glycosides, unsaturated glycosides by oxidation of . . . . Methylkasugaminide Methyl sulfoxide carbodiimide-pyridinium phosphate Methyl 1,2,3,4-tetra-O-acetyl-0-Dglucuronate Methyl a- and /?-D-xylopyranoside 2,4-phenylboronates Molecular ion Molecular weight determination . . . Musher and Corey Mycinose 61,

207 207 183 207 144 19 59 58 244 65 204 205 244 207

N

NBS, mechanism of bromination by Negative-ion mass spectra NMR of deoxy inositols Novel syntheses of deoxy sugars . . . Nucleosides, mass spectra of

185 205 47 141 205

O

Over-oxidation reaction of malonaldehyde 98 Over-oxidation reactions 94 Oxidation of 2-deoxyglycosides with ruthenium tetroxide 143 Oxidation of 2-deoxyglycosides with the chromium peroxide-pyridine complex 143 Oxidation of triose reductone by periodate 99 Oxygen, through the ring 244 P

Paramose Pentofuranosyl phosphate, 2-deoxya-D-erythro-

Pentopyranoside phenylboronates . . Pentose, 2-deoxy-D-ert/tfcro Pentose 5-phosphate, 2-deoxy-r> erythro Pentose 5-phosphate, 3-deoxy-Derythro Pentose 5-phosphate, 2-deoxy-Dthreo Pentose 5-phosphate, 3-deoxy-Lthreo Periodate oxidation 94, Periodate oxidation of dihydroxyfumaric and L-ascorbic acids . . Periodate titrations of deoxyinositols Phenylboronate esters Phenyllboronates, glycoside Phenylboronates, pentopyranoside . . Phenylboronic acid

207 79

64 95 73 77 76 77 207 100 51 65 64 64 64

Phosphate esters of (2-deoxy-D-Zt/xo-hexose) Phosphates, deoxy sugar Phosphonamide derivatives with alkyl halides, reaction of sugar Phosphorodiamide derivatives with alkyl halides, reaction of sugar Phosphorus-containing reagents, Preparing halodeoxy sugars using Phorphorus pentachloride in chloroform Phosphorous pentoxide Phosphorus tribromide and bromine Phosphorylated deoxy sugar acids . . Phosphorylated deoxy sugars Piricularia oryzae Polychlorinated sugars Proton magnetic resonance spectroscopy Pseudo-a-DL-galactopyranose Pseudo-/?-DL-gulopyranose Pseudo-hexoses Pseudomonas Pseudo-a-DL-talopyranose Pyranoid ring, ring expansion of a . Q Quantitative estimation of deoxy sugars Quercitol, protoQuercitol, scylloQuercitol, viboR Reactivity at C-4 in hexose sulfonates Reactivity at the C-4 position of hexose and hexoside sulfonates. Rearrangement of tetra-O-benzoyl-2hydroxy-D-glucal Rearrangements induced by substituted acetic acids Reduction of iodates by ene-diols . . Reduction of unsaturated acetates . Replacement of a sulfonate ester attached to a secondary carbon L-rhamnulose Ring-deoxy sugars, synthesis of . . . . Ring expansion of a furanoid ring . . Ring expansion of a pyranoid ring . Ring proton chemical shifts Ruthenium tetroxide oxidation of 2-deoxyglycosides by oxidation of sugar derivatives by .

71 109 178 178 172 192 191 60 191 88 70 15 181 228 53 53 51 16 52 148

94 44 47 42 168 165 153 156 100 153 163 78 51 146 148 249 56 143 142

S

Selective introduction of chlorine at C-6 with sulfuryl chloride Solvolysis of sulfonate esters, unexpected reactions during the Spin-decoupling Spin-tickling 229, Streptomyces kasugaensis


181 161 229 231

15

259


INDEX

Streptose Structure elucidation of deoxy sugars Substituted actic acids, rearrangements induced by Sulfonate ester attached to a secondary carbon, replacement of a Sulfonate esters, preparation of halodeoxy sugars by displacement of Sulfur monochloride Sulfuryl chloride, chlorodeoxy sugars by reaction with Sulfuryl chloride, selective introduction of chlorine at C-6 with . . Synthesis of deoxy sugars by hydrazino compounds by mercaptalation novel by tosylhydrazone Synthesis of desosamine Synthesis of halodeoxy sugars Synthesis of ring-deoxy sugars

122 206 156 163 160 197 179 181 145 145 141 144 167 159 51

T

TDP-a-D-glucose TDP-/?-L-rhamnose TDP-streptose 1,2,3,4-Tetra-O-acetyl-^-Dglucuronate, methyl Tetra-O-acetyl-2-hydroxy-D-glucal, isomerization of 1,2,3,4-Tetra-O-acetyl-^-D ribopyranose Tetra n-butylammonium fluoride . . . 2-Thiobarbituric acid-malonaldehyde adduct Tosyl chloride, chlorinated sugars by

121 121 122 244 151 244 162 98 164

Tosylhydrazone synthesis of deoxy sugars 2,3,4-Tri-0-acetyl-l,6-anhydro-/?-Dglucopyranose 3,4,6-Tri-O-acetyl-D-glucal 2,3,4-Tri-0-benzoyl-2-deoxy-/?-Darabino-hexoside Tri-O esters of 2-hydroxy-D-xylal, isomerization of Triose reductone by periodate, oxidation of Triphenylphosphine in carbon tetrachloride Triphenylphosphite dihalides Triphenylphosphite methiodide . . . . U Unexpected reactions during the solvolysis of sulfonate esters . . Unsaturated acetates, reduction of . Unsaturated glycosides by oxidation of methyl glycosides Unsaturated sugar derivatives, anomalies of Unsaturated sugars Uracil, l-(5-deoxy-a-Llyxofuranosyl) .

144 245 246 1 155 99 178 172 172

161 153 144 151 120 133

V

Vicinal coupling constants, angular dependence of

236

W

Webb and Levy test for 2-deoxy pentoses

96

X

D-xylal, isomerization of tri-O-esters of 2-hydroxy 155


A B C D

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