Tetra-O-benzoyl-a-D-mannopyranosyl

Similarly, the mannopyranosyl analog (346) was synthesized by condensation of di-O-isopropylidene-a-DL-carba-mannopyranose (349) with 348. The other isomer (347) was obtained by reaction of 278 with tetra-O-benzoyl-a-D-mannopyranosyl bromide (350). The four carba-glucopyrano-syl D-mannopyranosides, including 346 and 347, show no antiviral activity. 

C34H26C1209 2,3,4,6-Tetra-O-benzoyl-a-D-mannopyranosyl chloride (TBZMAC)125... 

Neighbouring group participation in trichloroacetimidate glycosylations glycosylation of 4,6-0-benzylidene-l,2-0-(/ /5 )-ethylidene-a-D-glucopyranose with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate [39]. 

Penta-O-benzoyl-a-D-mannopyranose dissolved at —10° in HF and kept for 30 min. tetra-O-benzoyl-a-D-mannopyranosyl fluoride. Y 85%. F. e. s. G. Pedersen, Acta Ghem. Scand. 17, 673 (1963). 

Benzoylated pyranoses also react smoothly with trimethylsilyl azide under SnCU catalysis. Treatment of penta-O-benzoyl-a-D-mannopyranose yields the l,2-tra ,s-configured product, 2,3,4,6-tetra-(9-benzoyl-a-D-mannopyranosyl azide (11), and not to the originally assumed p anomer. ... 

Regioselective debenzoylation of nucleoside 2, 3 5-tri-O-benzoates using hydrazine hydrate has been reported. With 1 mol reagent in acetic acid-pyridine the 3 5-di-O-benzoyl derivative was produced when the bases were adenine, guanine, or indole, whereas with excess hydrazine hydrate in 1 1 chloroform-methanol, 98% of the 5-O-benzoyl derivative was produced (base = adenine or uracil). 3, 5-Di-O-benzoyl-2-deoxy-nucleosides gave a 90% yield of a 1 1 mixture of 3 - and 5-O-benzoyl nucleosides with 1 mol hydrazine hydrate in pyridine. Treatment of the mannose orthoacetate (5) with benzoyl chloride in pyridine gave 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl chloride and ethylbenzoate, whereas the related orthoester of mu co-inositol (6) gave 66% of the correspond-... 

Acetylated and Benzoylated Derivatives of Sugars.—1,2,3,5-Tetra-O-acetyl-jS-D-ribofuranose, 3-0-acetyl-jS-L-arabinofuranose 1,2,5-orthobenzoate, (Z)-l-O-acetyl-2,3 4,5-di-0-isopropylidene-D-e/ y/Aw- and -D-/Areo-pent-l-enitol, 2,3,4-tri-O-benzoyl-jS-D-xylopyranosyl chloride, 2,3,4-tri-0-acetyl-j9-D-xyIopyranosyI azide, 1,3,4-tri-0-acetyl-2-deoxy-2-fluoro-a-D-xylopyranose, 1,2,3,4-tetra-O-acetyl-a-D-Iyxopyranose, 2,3,4,6-tetra-0-acetyl-a -D-glucopyranosyl bromide, 3,4,6-tri-0-acetyl-l,2-0-(l-cyanoethyIidene)-a-D-glucopyranose, 3,4,6-tri-O-acetyl-)S-D-mannopyranose l,2-(methyi orthoacetate), 2,3-di-0-acetyI-l,6-anhydro-jS-D-galactopyranose, 2,3,4,6-tetra-0-acetyl-j8-D-galactopyranosyl cyanide, 1,2,3,4,6-penta-O-acetyl-a-D-idopyranose, 1,4,5-tri-0-acetyl-2,3-0-isopropyIidene-)S-D-fructopyranose, and 2,3,4-tri-O-acetyl-a-L-rhamnopyrano-syl and 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl chlorides. ... 

Methyl 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-p-i>-galactopyranosyl)-a-i>allopyranoside, G-39 Methyl 3,4,6-tri-0-acetyl-2-S-(2,3,4,6-tetra-0-acetyl-a-D-glua>pyranosyl)-2-thio-p-D-glucopyranose, T-78 Methyl 2,4,6-tri-0-acetyl-3-0-(2,3,4,6-tetra-0-acetyl-a-D-mannopyranosyl)-a-D-mannopyranoside, M-93 Methyl 2,3,6-tri-0-benzoyl-4-0-(2,3,4,6-tetra-0-benzoyl-p-i>-galactopyranosyl)- p-i>-allopyranoside, G-40 Methyl 2,4,6-tri-0-l5enzyl-3-0-(3,4,6-tri-0-benzyl-P-D-mannopyraiiosy -a-D-mannopyranoside, M-97 Methyl p-turanopyranoside, T-201... 

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