Glucopyrano side

Benzyl 2-acetamido-6-0-benzyl-2,4-dideoxy-4-fluoro-a-D-glucopyrano-side and the corresponding free sugar were prepared from benzyl 2-acet-amido-3-0-allyl-6-0-benzyl- (or -3,6-di-0-benzyl)-2-deoxy-a-D-galacto-pyranoside by treatment with DAST (in diglyme). 

To study the binding mode of the yS-D-galactopyranosyl residue of the Lewis b human blood-group determinant to its monoclonal antibody or to a lectin, methyl 2-acetamido-2-deoxy-3-0-(6-deoxy-6-fluoro-2-0-a-L-fuco-pyranosyl-y -D-galactopyranosyl)-4-0-a-L-fucopyranosyl-/ -D-glucopyrano-side was synthesized. ... 

Besides di- and poly-saccharides, zeolites have been applied for hydrolysis of simple glycosides as described by Le Strat and Morreau.132 Methyl a- and /i-D-glucopyrano-sides were treated with water in the presence of dealuminated HY faujasite with an Si/Al ratio of 15, at temperatures ranging between 100 and 150 °C. It was observed that the reaction rate for the (i glycoside was about 5-6 times higher than that for the oc anomer, a result that might arise from the shape-selective properties of the zeolite and stereoelectronic effects on the surface of the solid. 

A. Basso, A. Ducret, L. Gardossi, and R. Lottie, Synthesis of octyl glucopyrano-side by almond /i-ghicosidase adsorbed onto Celite R-640 , Tetrahedron Lett., 43 (2002) 2005-2008. 

The regioselective esterification at position 6 of a-D-glucose and a-D-glucopyrano-sides with fatty acids [81] is readily achieved by use of Novozym 435, in accordance with Scheme 8.56. 

Proof of Constitution.—Since the crystalline a- and 8-forms of 3,4,6-trimethyl-D-glucose, isolated by Sundberg and coworkers,28 were each obtained by hydrolysis of methyl 3,4,6-trimethyl-/3-D-glucopyrano-side,82,154 the proof of the constitution of this glucoside obviously played an important part in the characterization of the trimethylglucose itself. Unfortunately, there is no such crystalline reference compound to correlate the earliest samples of sirupy 3,4,6-trimethyl-D-glucose157,168 with the crystalline specimens isolated by Sundberg and coworkers. 

Sunnerheim-Sjoberg, K. (1992). (IS, 2R, 4S, 5S)-Angelicoidenol-2-0-/S-D-glucopyrano-side a moose deterrent compound in Scots pine [Pinus sylvestris L.). Journal of ChemicalEcobgy 18,2025-2039. 

W. Hakamata, T. Nishio, and T. Oku, Synthesis of p-nitrophenyl 3- and 6-deoxy-a-D-glucopyrano-sides and their specificity to rice a-glucosidase, J. Appl. Glycosci., 46 (1999) 459—463. 

Methyl 4,6-0-ethylidene-2,3-di-0-p-tolylsulfonyl-a-D-glucopyrano-side affords the D-alio epoxide as readily as the benzylidene analog,26 contrary to an earlier report of its stability at room temperature.27... 

The parsley plant, Petroselinum crispum, for example, contains at least two of the D-apiose flavonoids, namely, apiin 4, 5-dihydroxy-flavon-7-yl 2-0- [3-C (hydroxymethyl)-/3-D-erythrofuranosyl] -/3-D-glucopyranoside (4) and petroselinin 3, 4, 5-trihydroxyflavon-7-yl 2-0- [3-C-(hydroxymethyl)-/3-D-erythrofuranosyl]-/3-D-glucopyrano-side. 1 The principal compound containing D-apiose in parsley... 

Imidazole-l-sulfonate Displacements at the C-3 and C-4 Positions of Sngar Derivatives. Displacement reactions of tosylates at the C-3 position of a-D-glucopyrano-side derivatives proceed with difficulty because of a nonbonded 1,3-diaxial interaction between the aglycone and the approaching nucleophile [32], as well as complications arising from neighboring group participation [90],... 

When D-glucose is treated with acidic methanol, the first products which can be isolated are mainly methyl furanosides, but after extensive reaction the furanosides disappear and methyl glucopyrano-sides accumulate. Why ... 

The first of these methods involves the reaction of triphenyl phosphite methiodide with methyl 3-0-methyl-2-0-p-tolylsulfonyl-a-D-glucopyrano-side, hydrogenation of the resulting 4,6-diiodo derivative, and hydrolysis,186 as adapted to monosaccharides by Kochetkov and coworkers.1,0 In another approach,281 ethyl 2,3-anhydro-4,6-dideoxy-D-nbo-hexopyranoside, obtained from desosamine, was treated with sodium methoxide, to give a mixture of 2- and 3-methyl ethers. After fractionation and separation of side products,288 the 3-methyl ether was hydrolyzed, to give crystalline chalcose. McNally and Overend800 have described another synthesis, starting from methyl 4-deoxy-D-xj/Zo-hexoside.107... 

---