Arabinopyranoside methyl 3,4-0-isopropylidene

The bis(methyl 3, 4-0-isopropylidene- 9-D-arabinopyranoside) 2,2 -car-bonate obtained by Foster and Wolfrom from methyl 3,4-0-isopropyli-... 

In their study of the reactions of methyl 3,4-0-isopropylidene-2-0-(sodium thiolthiocarbonyl)-/3-D-arabinopyranoside, Foster and Wolfrom showed that when bis(methyl 3,4-0-isopropylidene-/3-D-arabinopyranoside) 2,2 -thionocarbonate (VI) was treated with mercuric oxide, bis(methyl 3,4-0-isopropylidene-j8-D-arabinopyranoside) 2,2 -carbonate was produced. 

In the same year, Wolfrom and Foster synthesized certain 2-0-[(alkyl-thio)thiocarbonyl] derivatives of methyl 3,4-0-isopropylidene-iS-D(and l)-arabinopyranoside and of methyl 4,6-0-benzylidene-3-0-methyl- -D-altro-pyranoside by the action of carbon disulfide on the appropriate 2-0-sodio compounds, followed by treatment with an alkyl halide. The halides used— methyl iodide and triphenylmethyl iodide—were chosen for their ability to cause (S-alkylation rather than transformation to a thionocarbonate (see p. 110). The D- and L-arabinose derivatives could be converted to 2-deoxy-o-eri/ /iro-pentose (see p. 141). 

More recently, Wolfrom and Foster found that the d and l enantio-morphs of methyl 3,4-0-isopropylidene-2-0-[(methylthio)thiocarbonyl]-/3-arabinop3Tanoside rearrange, on pyrolysis, to the appropriate 2-methyl-thio)carbonyl] esters. The reductive desulfurization of methyl 3,4-0-isopropylidene-2- S - [(methylthio)carbonylj - 2 - thio -/3 - d - arabinopyranoside (LXVIII) with Raney nickel, to afford a low yield of methyl 2-deoxy-3,4-0-isopropylidene-/3-D-erj/intramolecular rearrangement to LXVIII, and the relationship of the transformation to the Chugaev reaction was discussed. 

Aiabinofuranose, 3,6 -di - 0 - (methoxy-carbonyl)- ,-, 1,2-carbonate, 108 Arabinogalactan, 73, 74 fractional precipitation of, 55 purification of, 56 Arabinonic acid, D-, formation of 3-deoxy-D-oro5fno-heptu-losonic acid 7-phosphate from, 253 Arabinopyranoside, bis (methyl 3,4-0-isopropylidene - /3 - n -, 2,2 - carbonate, 118, 132 2,2 -thionooarbonate, 132, 133 —, methyl 3,4-0-isopropylidene-/J-n-, 118, 119... 

Carbohydrates, allyloxycarbonates, 123 carbonates of, 151 chloroformyl esters of, 102 conformational analysis of, 12 reaction of, with carbon dioxide, 129 with carbon disulfide, 135 with carbonic acid, 129 with phosgene in acetone, 105 thermochemical properties of, 21 thiocarbonates of, 157 Carbonic acid, esters, 91,92,151 bis(methyl 3,4-0-isopropylidene-/3-D-arabinopyranoside), 2,2 -, 96 bis(1,2,3,4 - tetra - O - acetyl -/J - D - glucose), 6,6 -, 104 cyclic, 103... 

The resistance of the tertiary hydroxyl group of methyl 3,4-0-isopropylidene-2-0-methyl-/3-L-arabinopyranoside to esterification with p-toluenesulfonyl chloride in pyridine at room temperature was overcome " by first forming the sodio derivative in ether and then treating this with p-toluenesulfonyl chloride in ether. 

C-(cis-phenylethenyl) analogs was unsuccessful, and the tertiary alcohol group was regenerated methyl 3,4-0-isopropylidene-2-0-p-tolylsuIfonyl-2-C-vinyl-j8-L-arabinopyranoside (3, R = CH=CH2, R = OTs) gave a mixture of 70% of the parent alcohol and 30% of a deoxy sugar (4) in which the vinyl double bond of compound 3 had... 

Overend and coworkers oxidized methyl 3,4-0-isopropylidene-/3-L-arabinopyranoside with chromium trioxide/pyridine to give methyl 3,4-0-isopropylidene- 8-n- n/fAro-pentopyranosidulose (89). The preparation of a series of branched-chain compounds originating from this keto compound is described later (see p. 282). In other (unreported) experiments, methyl... 

The trichloroethylidene acetals 12, phenyl 2,3,4,6-tetra-C -acetyl-P-D-galacto-pyranoside, benzyl P-L-arabinopyranoside and its 3,4-D-isopropylidene and 2-0-benzoyl-3,4-0-isopropylidene derivatives. p-Nitrophenyl a-D-mannopyrano-side, 3-deoxy-3-C-(ethoxycarbonyl)methyl-1,2 5,6-di-0-isopropylidene-a-D-... 

O-Isopropylidene, 2-mesyl Methyl 3,4-O-isopropylidene-2-O-mesyl-p-D-arabinopyranoside... 

Benzoyl Methyl 2-0-benzoyl-3,4A)-isopropylidene-p-L-arabinopyranoside C16H20O6 308.33... 

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 2-0-acetyl-3,4-0-isopropylidene-p-D-arabinopyranoside, M-153 Methyl 2-0-acetyl-3,4-0-isopropylidene-p-L-arabinopyranoside, M-I97 Methyl 2-0-acetyl-3,4-0-isopropylidene-a-L-fucopyranoside, M-19S Methyl 2-0-acetyl-3,4-0-isopropylidene-a-D-galactopyranosiduronamide, M-188... 

Methyl 2- O -benzoyl-3-bromo-2,6-dideoxy-a-L-altropyranoside, B-106 Methyl 2-0-benzoyl-6-chloro-6-deoxy-a-D-glucopyranoside, C-88 Methyl 2- O -benzoyl-3-chloro-3-deoxy-5- O -trityl- p-D-xylofuranoside, C-109 Methyl 4- O -benzoyl-6-deoxy-2,3-di- O -methyl-a-D-altropyranoside, D-37 Methyl 6-0-benzoyl-2-deoxy-p-D-/yxo-hexopyranoside, D-202 Methyl 5-0-benzoyl-3-deoxy-3-iodo-a-D-arabinofuranoside, D-250 Methyl 4-0-benzoyl-2-deoxy-2-iodo-p-L-arabinopyranoside, D-249 Methyl 4- O -benzoyl-6-deoxy-6-iodo-2,3- O -isopropylidene-a-D-mannopyranoside, D-266... 

Methyl 2-0-benzyl 4,6-dideoxy-a-D-Wfeo-hexopyranoside, D-614 Methyl (benzyl p-D-glucopyranosid)uronate, B-17 Methyl (benzyl 2,3-0-isopropylidene-p-D-ribofuranosid)uronate, R-146 Methyl (benzyl 2,3,4-tri-0-acetyl-p-D-glucopyranosid)uronate, B-17 Methyl (benzyl 2,3,4-tri-0-benzyl-p-D-glucopyranosid)uronate, B-17 Methyl (benzyl 4,5,7-tri-0-benzyl-a-D-g/Mco-2-h tulopyranosid)onate, H-64 Methyl 2-0-benzyl-p-D-arabinofuranoside, M-152 Methyl 2-0-benzyl-p-L-arabinopyranoside, M-153... 

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-deoxy-4,5-0-isopropylidene-7-0-trityl-D-a//o-heptonate, A-532 Methyl 6-deoxymannofuranoside, M-206 Methyl 6-deoxymannopyranoside, M-207 Methyl 6-deoxy-4-0-mesyl-a-D-talopyranoside, D-372 Methyl 3-deoxy-3-(A-methylacetamido)-a-D-arabinofuranoside, D-293 Methyl 3-deoxy-3-(A-methylacetamido)-p-D-xylopyranoside, D-294 Methyl 6-deoxy-2-0-methyl-a-D-allopyranoside, D-34 Methyl 6-deoxy-3-0-methyl-a-D-allopyranoside, D-34 Methyl 6-deoxy-2-0-methyl-p-D-allopyranoside, D-34 Methyl 6-deoxy-3-0-methyl-p-D-allopyranosyl-(l 4)-2-deoxy-a-D-arabino -hexopyranoside, D-774 Methyl 6-deoxy-4-0-methyl-a-D-altropyranoside, D-37 Methyl 6-deoxy-4-0-methyl-p-D-altropyranoside, D-37 Methyl 3-deoxy-3-(methylamino)-a-D-arabinofuranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-D-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-L-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-p-L-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-D-xylopyranoside, D-294 Methyl 3-deoxy-3-(methylamino)-p-D-xylopyranoside, D-294 Methyl 3-deoxy-3-(methylamino)-p-L-xylopyranoside, D-294 Methyl 6-deoxy-4-0-methyl-a-D-glucopyranoside, D-142 Methyl 6-deoxy-3-0-methyl-a-D-glucopyranoside, D-142 Methyl 6-deoxy-3-0-methyl-p-D-glucopyranoside, D-142 Methyl 3-deoxy-3-C-methyl-a-D-glucopyranoside, D-301... 

Methyl 2,3-di-0-acetyl-4-deoxy-a-D-//ir o-hex-4-enopyranoside, D-181 Methyl 3,4-di-O -acetyl-2-deoxy-2-iodo-a-D-arabinopyranoside, D-249 Methyl 3,4-di-O -acetyl-2-deoxy-2-iodo-a-L-arabinopyranoside, D-249 Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo-a-D-lyxopyranoside, D-263 Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo-a-L-lyxopyranoside, D-263 Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo- D-ribopyranoside, D-270 Methyl 2,4-di-0-acetyl-3-deoxy-3-iodo-a-L-xylopyranoside, D-280 Methyl 2,4-di-0-acetyl-3-deoxy-3-iodo-p-L-xylopyranoside, D-280 Methyl 5,7-di-0-acetyl-6-deoxy-2,3-0-isopropylidene-p-L-gM/o heptofuranoside, D-162... 

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