Glucopyranoside methyl 3-0-benzoyl-4,6-0-benzylidene

This class of acylating agents has thus far been but little used in carbohydrate chemistry. However, unimolar benzoylation of methyl 4,6-O-benzylidene-a-D-glucopyranoside, methyl 4,6-O-benzylidene-a-D-altropyranoside, and benzyl 4,6-O-benzylidene-jS-D-galactopy-ranoside with benzoyl cyanide gave good yields of the corre-... [Pg.45]

Acyl migration is a reversible process, and external factors (for example, solubility) can influence the equilibrium. Thus, after dissolution of methyl 2-0-benzoyl-4,6-0-benzylidene-a-D-glucopyranoside in acetone-aqueous sodium hydroxide, almost immediate crystallization of the 3-benzoate occurred, in 65% yield.549 Similarly, benzyl 3-0-benzoyl-4,6-0-benzylidene-/3-D-galactopyranoside yielded the 2-... [Pg.101]

Methyl 3-benzamido-4,6-di-0-benzoyl-2,3-dideoxy-2-fluoro-a-D-al-tropyranoside (87) was obtained by treatment of methyl 2-benzamido-4,6-0-benzylidene-3-0-p-tolylsulfonyl-a-D-glucopyranoside (84) with tetrabutylammonium fluoride in hexamethylphosphoric triamide, followed by O-debenzylidenation and benzoylation.85 The reaction is... [Pg.240]

Takeo, K. Shibata, K., Regioselective Alkylation, Benzoylation, and Para-Toluene Sulfonylation of Methyl 4,6-0-Benzylidene-Beta-D-Glucopyranoside. Carbohydr. [Pg.43]

Methoxy-7-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene 2-Naphthalene-carboxylic acid, 5,6,7,8-tetrahydro-3-methoxy-, methyl ester (78112-34-2), 65, 98 Methyl acrylate (96-33-3), 66, 54, 59 dimerization by Pd(II), 66, 52 Methylamine, N-benzylidene-, 65, 140 METHYL 4-0-BENZOYL-6-BROMO-6-DEOXY-a-0-GLUCOPYRANOSIDE ... [Pg.251]

The structures of partially benzoylated derivatives of 1,6-anhydro-4, 6 -0-benzylidene-/3-maltose were established by methylation studies.51 During the course of this investigation, 2,3- and 3,3 -di- and 2,3,3 -tri-methyl ethers of l,6-anhydro-4, 6 -0-benzylidene-/3-maltose were prepared by using diazomethane-boron trifluoride etherate reagent. Methyl [methyl 2,3-di-0-methyl-4-0-(2,3,4,6-tetra-0-methyl-a -D-glucopyranosyl)-/3-D-glucopyranosid]uronate (15) has been synthe-... [Pg.222]

S. Hanessian 243 6-BR0M0-6-DE0XY HEXOSE DERIVATIVES BY RING-OPENING OF BENZYLIDENE ACETALS WITH N-BROMOSUCCINIMIDE METHYL 4-0-BENZOYL-6-BROMO-6-DEOXY-a-D-GLUCOPYRANOSIDE... [Pg.294]

Attempted sodium hydride mediated benzylation of methyl 3-0-benzoyl-4,6-0-benzylidene-P-D-galactopyranoside failed due to a benzoyl migration [65]. The acyl group migration and removal are also responsible for only 62 % yield of benzyl 2-acetamido-3,6-di-0-acetyl-4-0-benzyl-2-deoxy-a-D-glucopyranoside. Thallium eth-oxide instead of sodium hydride or alkoxide successfully restrained the acetyl group migration in this reaction [35]. [Pg.215]

Y. Ishido and N. Sakairi, Nucleophilic substitution reactions at C-2 of methyl-3-O-benzoyl-4,6-0-benzylidene-2-C)-(trifiuoromethylsulfonyl)-a-D-glucopyranoside, Carbohydr. Res. 97 151 (1981). [Pg.80]

A mixture of 4.98 g methyl 2-benzoyl-3-phenoxythiocarbonyl-4,6-benzylidene-a-D-glucoside (9.5 mmol), 7.40 mL allyltributyltin (23.9 mmol), 313 mg AIBN, and 15 mL toluene was refluxed for 4 h at which point TLC showed complete consumption of the starting material. The solution was concentrated, and the residue was flash chromatographed on silica gel using 5% EtOAc in toluene as the eluent to give 3.48 g methyl (3S)-2-0-benzoyl-4,6-di-0-benzylidene-3-allyl-3-deoxy-Q -D-glucopyranoside as a solid, in a yield of 62%, m.p. 138-139 C, Rf = 0.38 (EtOAc/hexanes, 1 9). [Pg.1598]

O-Benzylidene, 3-benzoyl Methyl 2-benzamido-3-0-benzoyl-4,6-0-benzyli-dene-2-deoxy-a-D-glucopyranoside C28H27NO7 489.524... [Pg.727]

Dibenzoyl Methyl 2,3-di-0-benzoyl-4,6-0-benzylidene-p-D-glucopyranoside C28H26O8 490.509 Mp 185°. [a]o +15.8 (CHCI3). [Pg.731]

Me glycoside, 4,6-O-benzylidene, 2-ben-zoyl Methyl 2-0-benzoyl-4,6-0-benzyli-dene-l-thio-p-D-glucopyranoside [38992-99-3]... [Pg.915]

Benzyl 2-benzamido-2-deoxy-3,4,6-tri-0-methyl-a-D-glucopyranoside, B-13 Benzyl 2-benzamido-2-deoxy-3,4,6-tri-0-methyl-p-D- ucopyranoside, B-13 Benzyl 2-benzamido-2,5-di(leoxy-a-D-ribofiiranoside, A-413 Benzyl 2-benzamido-3,4,6-tri-0-benzyl-2-deoxy-p-D-glucopyranoside, B-13 Benzyl 2-0-benzoyl-4,6-0-benzylidene-p-D-galactopyranoside, B-15 Benzyl 3-0-benzoyl-4,6-0-benzylidene-p-D-galactopyranoside, B-15 Benzyl 3- O -benzoyl-4,6- O -benzylidene-2- O - tosy 1- p-D-galactopyranoside, B-15... [Pg.1013]

Methyl 2-0-acetyl-4-0-benzoyl-a-D-ri6o-hexopyranosid-3-ulose, H-101 Methyl 3-0-acetyl-2-0-benzyl-4,6-0-benzylidene-a-D-glucopyranoside, M-164... [Pg.1072]

Methyl 2-0-benzoyl-4,6-0-benzylidene-a-D-galactopyranoside, M-162 Methyl 3-0-benzoyl-4,6-0-benzylidene-a-D-galactopyranoside, M-162 Methyl 2-0-benzoyl-4,6-0-benzylidene-p-D-galactopyranoside, M-163 Methyl 3-0-benzoyl-4,6-0-benzylidene-p-D-galactopyranoside, M-163 Methyl 6-O-benzoyl-3,4-0-benzylidene-a-D-galactopyranoside, M-185 Methyl 2-0-benzoyl-4,6-0-benzylidene-a-D-glucopyranoside, M-164 Methyl 3-0-benzoyl-4,6-0-benzylidene-a-D-glucopyranoside, M-164 Methyl 2-O-benzoyl-4,6-O-benzylidene-a-D-araZ mo -hexopyranosid-3-ulose oxime, H-95... [Pg.1075]

Methyl 5-0-benzoyl-2,3-0-benzylidene-p-D-ribofuranoside, M-208 Methyl 3-0-benzoyl-4,6-benzylidene-2-0-(2,3,4,6-tetra-0-acefyl-p-D-glucopyranosyl)-p-D-allopyranoside, G-277 Methyl 2-0-benzoyl-4,6-0-benzylidene-l-thio-p-i>glucopyranoside, T-70 Methyl 3-0-benzoyl-4,6-0-benzylidene-l-thio-p-i>glucopyranoside, T-70 Methyl 2-0-benzoyl-4,6-0-benzylidene-3-0-tosyl-a-D-altropyranoside, M-156... [Pg.1075]

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