Lyxofuranoside, methyl 2,3-0-isopropylidene

DL-Dihydrostreptose and its ribo isomer were similarly obtained. Birch reduction of 2-methyl-3-furoic acid, followed by addition of methanol, bromination, and dehydrobromination, gave 402 as a mixture of the isomers. Hydroxylation of 402 with osmium tetraoxide-so-dium chlorate, and subsequent treatment with acetone-sulfuric acid afforded three isomeric acetals (403-405). The structures of these compounds were assigned on the basis of their H-n.m.r. spectra. In addition, the relationship between 403 and 404 was established by hydrolysis and reglycosidation. The methyl esters 403-405 were quantitatively reduced to the corresponding alcohols. The mixture of alcohols obtained from 403 and 404 was converted into crystalline 5-deoxy-3-C-(hydroxymethyl)-l,2-0-isopropylidene-a-DL-ribofuran-ose (406), which was compared directly with a sample prepared from D-xylose. Methyl 5-deox y-3-C-(hydroxy methyl)-2,3-O-isopropy lidene-/3-DL-lyxofuranoside (407), obtained by reduction of 405 with lithium aluminum hydride, was hydrolyzed with dilute hydrochloric acid, to give a,/3-DL-dihydrostreptose.2,ifi... 

Compound 177 was purified through the corresponding methyl /3-L-glucopyranoside by treatment with methanol, ether, and silver carbonate (overall yield 42%). The same reaction was applied186 to methyl 5-0-benzoyl-2,3-0-isopropylidene-a-D-lyxofuranoside (178), which gave the bromide 180 (crude yield 98%). Evidently, com-... 

The deamination of the pentoside methyl 4-amino-4-deoxy-2,3-0-isopropylidene-a-D-lyxofuranoside paralleled that of the mannopy-ranoside 39a in that substitution (with inversion) and ring contraction occurred to give a-D-Iyxopyranoside (60%) and /B-l.-ribofuranoside (40%) derivatives as products.1243 In contrast, there was no ring... 

Me glycoside, 5-benzyl Methyl 5-O-benzyl-2,3-O-isopropylidene-a-D-lyxofuranoside [32780-15-7]... 

Me glycoside, 2,3-isopropylidene, 5-S-v4c. Methyl 5-S-acetyl-2,3-0-isopropylidene-5-thio-a-D-lyxofuranoside C11H18O5S 262.326 Cryst. (MeOH aq.). [a]o +65 (c, 1.2 in CHCI3). 

Benzyl 2,3-0-isopropylidene-a-D-lyxofuranoside, 1-70 Benzyl 2,3-0-isopropylidene-p-D-lyxofuranoside, L-72 Benzyl 2,3-0-isopropylidene-a-D-mannofuranoside, B-19 Benzyl 2,3-0-isopropylidene-a-D-mannopyranoside, B-19 Benzyl 2,3-0-isopropylidene-5-0-mesyl-a-D-lyxofuranoside, 1-70 Benzyl 2,3-0-isopropylidene-6-0-mesyl-a-D-mannofuranoside, B-19 Benzyl 2,3-0-isopropylidene-4-0-mesyl-a-L-rhamnopyranoside, B-20 Benzyl 3,4-0-isopropylidene-2-C-methyl-p-L-arabinopyranoside, M-229 Benzyl 3,4-0-isopropylidene-2-C-methyl-p-L-ribopyranoside, M-286 Benzyl 3,4-0-isopropylidene-2-0-methyl-p-D-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-2-0-methyl-p-L-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-p-D- /7// ro-pentopyranosid-2-ulose, P-42 Benzyl 2,3-0-isopropylidene-a-L-rhamnopyranoside, B-20 Benzyl 2,3-0-isopropylidene-p-D-ribofuranuronoside, R-146 Benzyl 3,4-0-isopropylidene-p-D-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-p-L-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-2-0-(2,3,4,6-tetra-0-acetyl-p-D-glucopyranosyl)-p-D-arabinopyranoside, G-284 Benzyl 2,3-0-isopropylidene-5-0-(2,3,4,6-tetra-0-acetyl-p-D-glucopyranosyl)-p-D-ribofuranoside, G-462 Benzyl 3,4-0-isopropylidene-2-0-tosyl-a-D-arabinopyranoside, B-14 Benzyl 3,4-0-isopropylidene-2-tosyl-p-L-arabinopyranoside, B-14 Benzyl 3,4-0-isopropylidene-2-0-(2,3,5-tri-0-benzoyl-a-L-arabinofuranosyl)-p-L-arabinopyranoside, A-801 Benzyl 3,4-0-isopropylidene-6-0-trityl-p-D-galactopyranoside, B-15... 

Methyl 4-0-acetyl-2,3-0-isopropylidene-a-L-rhamnopyranoside, M-207 Methyl 5-5-acetyI-2,3-0-isopropylidene-5-thio-a-D-lyxofuranoside, T-80 Methyl 5-5-acetyI-2,3-0-isopropylidene-5-thio-a-L-rhamnofuranoside, T-88 Methyl 4-0-acetyI-2,3-0-isopropylidene-l-thio-p-D-xylopyranoside, T-98 Methyl 2-0-acetyI-4,6-0-isopropylidene-3-0-tosyl-a-D-gulopyranoside, M-194... 

Methyl 2-0-benzyl-3,4-0-isopropylidene-p-L-arabinopyranoside, M-197 Methyl 2-0-benzyl-3,4-O-isopropylidene-a-L-fucopyranoside, M-198 Methyl 3- 0 -benzyl-1,2- O -isopropylidene- p-L-idofuranuronate, 1-12 Methyl 5-0-benzyl-2,3-0-isopropylidene-a-D-lyxofuranoside, 1-70 Methyl 5-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 6-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 4-O-benzyl-2,3-O-isopropylidene-a-L-rhamnopyranoside, M-207 Methyl 2-O-benzyl-3,5-O-isopropylidene-a-D-xylofuranoside, M-216 Methyl 2-O-benzyl-3,5-O-isopropylidene-p-D-xylofuranoside, M-216 Methyl 3-0-benzyl-2-0-methyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-2-0-methyl-a-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 5-0-benzyl-2-0-methyl-p-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 2,6-0-benzyl-3-0-methyl-a-D-mannopyranoside, M-271 Methyl 3-0-benzyl-2-O-methyl-6-0-tosyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-3-0-methyl-a-D-xylofuranoside, M-216 Methyl 3-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 4-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 3-0-benzyl-p-L-ribofuranoside, M-208 Methyl 3-O-benzyl-4-O -(2,3,4-tri-O-benzyl-p-D-xylopyranosyl)-p-D-xylopyranoside, X-80... 

Methyl 2,3-0-isopropylidene-p-D-lyxofuranoside, 1-70 Methyl 2,3-0-isopropylidene-L-lyxopyranoside, 1-70 Methyl 2,3-0-isopropylideiie-a-D-lyxopyranoside, M-202 Methyl 2,3-0-isopropylidene-a-D-mannofnranoside, 1-71 Methyl 2,3-0-isopropylidenemannopyranoside, M-200 Methyl 3,4-0-isopropylidene-2-0-mesyl-a-D-arabinopyranoside, M-153 Methyl 3,4-0-isopropylidene-2-0-mesyl-p-D-arabinopyranoside, M-153 Methyl 2,3-0-isopropylidene-6-0-mesyl-a-D-/Kxo-hexopyranosid-4-ulose, H-99... 

Methyl 5-0-benzoyl-2,3-di-0-tosyl-fl-D-Iyxofuraiioside, M-201 Methyl 5-5 -benzoyl-2,3-0-isopropylidene-5-thio-a-i>tyxofiiraiioside, T-80 Methyl 5-0-benzyl-2,3-0-isopropylidene-a-i>tyxofiiraiioside, 1-70 Methyl 4-bromo-4-deoxy-D-lyxopyranoside, B-84 Methyl 5-chloro-5-deoxy-a-D-lyxofuranoside, C-96 Methyl 2-chloro-2-deoxy-p-D-lyxopyranoside, C-95 Methyl 4-deoxy-2,3-di-0-mesyl-4-( -dimethylainiiio)-a-L-lyxopyranoside, A-298... 

Methyl 5-bromo-5-deoxy-2,3- 0 -isopropylidene-a-D-ribofuranoside, B-93 Methyl 5-chloro-5-deoxy-a-L-idofuranosidurono-6,3-lactone, C-90 Methyl 5-chloro-5-deoxy-2,3-0 -isopropylidene-p-D-ribofuranoside, C-100 Methyl 5-chloro-5-deoxy-a-D-lyxofuranoside, C-96 Methyl 5-chloro-5-deoxy-a-D-ribofuranoside, C-100 Methyl 5-chloro-5-deoxy-p-D-ribofuranoside, C-100 Methyl 5-deoxy-5-iodo-2,3-0-isopropylidene-p-D-ribofuranoside, D-272 Methyl 2,3-di-0-benzoyl-5-bromo-5-deoxy-p-D-ribofuranoside, B-93 Methyl 1,2,3,4-tetra-O -acetyl-5-bromo-p-D-glucopyranuronate, B-117... 

Methyl 4-amino-4-deoxy-5-thio-p-L-Iyxopyranoside, A-350 Methyl 3-amino-3-deoxy-5-thio-a-D-xyIopyranoside, A-352 Methyl 5-5-benzoyl-2,3-0-isopropyIidene-5-thio-oc-D-lyxofuranoside, T-80 Methyl 6-deoxy-2,3-0-isopropylidene-5-thiobenzoyl-a-L-talofuranoside, D-379... 

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