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Lyxofuranoside methyl 2,3-anhydro

For furanoid derivatives, 2,3-epoxides are readily formed from trans-related groups. Other stereochemical features do not appear to be important, and this reflects the mobility of the orientations on such five-membered rings. Here, eclipsing polar interactions between cis sulfonate and methoxyl groups are not likely to alter much on passing to the transition state and, accordingly, both anomers of methyl 2-O-methylsulfonyl-D-xylofuranoside form the 2,3-anhydro-D-lyxofuranoside on treatment22 with sodium methoxide at 0°. [Pg.116]

V. S. Murthy, A. S. Gaitonde, and S. P. Rao, One-pot conversion of 1,2-diols to epoxides —convenient preparation of methyl 2,3-anhydro-5-0-trityl-/ -D-lyxofuranoside and methyl 2,3-anhydro-4,6-0-benzylidene-a-D-mannopyranoside, Synth. Common., 23 (1993) 285-289. [Pg.183]

In connection with carbohydrates, (1,5,3,5,5W)-1,3-dimcthyl-2,9-dioxabicyclo 3.3.11 nonane has been prepared from dithiane and D-glucose263. An epoxide derived from D-xylose 195 has been opened regioselectively by means of compound 161 at the 4-position in 90% yield264. In the case of the methyl 2,3-anhydro-a-D-lyxofuranoside 196 the ring... [Pg.171]

Methyl 5-0-acetyl-2,3-anhydro-a-D-lyxofuranoside MgBrj 3-substituted n-arabinose — 57... [Pg.188]

Methyl 2,3-anhydro-5-0-benzyl-tt-D-lyxofuranoside KHFs 3-substituted d-arabinose — 64a... [Pg.191]

C-3 in pentose derivatives, with ammonia as the attacking group, have been recorded. An exception to this general behavior was noted in the reaction of methyl 2,3-anhydro-/3-D-lyxofuranoside with benzylthiolate anion, which gave a 60% yield of the 2-thio-D-xylose derivative and a 40% yield of the 3-thio-D-arabinose isomer. [Pg.175]

Application of the azidomercuration-demercuration procedure to the 5-ene (9) gave the 6- and 5-azides (10) and (11) in the ratio 1 4 (Scheme 1). The synthesis of azido-sugars via 2,3-anhydro-furanosides has been reported. Methyl 2,3-anhydro-0 -D-lyxofuranoside (12) gave the 3-azide (13) in 95% yield, and its 5-0-tosyl ester (14) gave the 3,6-diazide (15) in 84% yield. In contrast, the 2,3-anhydro-riboside (16) gave a mixture of the 2- and 3-azides (17) and (18) in the ratio 3 2. However, substitution at C-5 of (16) resulted in steric hindrance of the approach to C-3 and consequently the 5-tosylate (19) afforded the 2,6-... [Pg.91]

Me glycoside, 5-tosyl Methyl 2,3-anhydro-5-O-tosyl-a-D-lyxofuranoside [66108-03-0]... [Pg.139]

Me glycoside, 5-Me Methyl 2,3-anhydro-5-O-methyl-P-D-lyxofuranoside C7H12O4 160.169 Mp 14-15°. Md -88 (H2O). [Pg.139]

Methyl 2-0-acetyl-3,4-anhydro-a-D-arabinopyranoside, A-504 Methyl 2-0-acetyl-3,4-anhydro-p-L-arabinopyranoside, A-504 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-p-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-mannopyranoside, A-687 Methyl 4-0-acetyl-3,6-anhydro-a-D-galactopyranoside, A-620 Methyl 5-0-acetyl-2,3-anhydro-a-D-lyxofuranoside, A-664 Methyl 5-0-acetyl-2,3-anhydro-p-D-lyxofuranoside, A-664 Methyl 3-0-acetyl-2,6-anhydro-4-0-methyl-p-D-mannopyranoside, A-678 Methyl 4-0-acetyl-2,3-anhydro-a-D-rhamnopyranoside, A-687 Methyl 5-0-acetyl-2,3-anhydro-a-D-ribofuranoside, A-690 Methyl 5-0-acetyl-2,3-anhydro-p-D-ribofuranoside, A-690 Methyl 4-0-acetyl-2,3-anhydro-p-D-ribopyranoside, A-693 Methyl 4-0-acetyl-2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2-0-acetyl-p-L-arabinopyranoside, M-153 Methyl 3-0 -acetyl-2-azido-4,6-0 -benzylidene-2-deoxy-a-D-mannopyranoside, A-912... [Pg.1072]

Methyl 2,3-anhydro-6-0-trityl-a-D-allopyranoside, A-484 Methyl 3,4-anhydro-6-0-trityl-a-D-altropyranoside, A-495 Methyl 2,3-anhydro-6-0-trityl-a-D-gulopyranoside, A-639 Methyl 2,3-anhydro-5-0-trityl-a-D-lyxofuranoside, A-664 Methyl 2,3-anhydro-5-0-trityl-p-D-lyxofnranoside, A-664 Methyl 2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2,3-anhydro-5-0-trityl-a-D-ribofnranoside, A-690 Methyl 2,3-anhydro-5-0-trityl-p-D-ribofnranoside, A-690 Methyl 3,5-anhydro-p-D-xylofuranoside, A-728 Methyl p-D-apiofuranosyl-(l ->6)-p-D-glucopyranoside, A-784 Methyl arabinofuranoside, M-152... [Pg.1074]

Oxirans. - Methyl a-D-glucopyranoside has been oxaphosphoranylated with diethoxytriphenylphosphorane and the product mixture was thermolysed to give epoxides (18) and (19). The thermolysis was accelerated by the presence of LiBr, and in this case only epoxide (18) was obtained. An improved five-step synthesis of methyl 2,3-anhydro-a- and P D-lyxofuranosides from D-xylose reports no need for intermediary purifications. ... [Pg.81]


See other pages where Lyxofuranoside methyl 2,3-anhydro is mentioned: [Pg.213]    [Pg.8]    [Pg.18]    [Pg.159]    [Pg.151]    [Pg.431]    [Pg.16]    [Pg.170]    [Pg.193]    [Pg.247]    [Pg.32]    [Pg.139]    [Pg.139]    [Pg.139]    [Pg.1073]    [Pg.1074]    [Pg.1155]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.1156]    [Pg.86]    [Pg.392]    [Pg.58]   
See also in sourсe #XX -- [ Pg.116 ]

See also in sourсe #XX -- [ Pg.25 , Pg.116 ]




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