Anhydridization of 1-Deoxy-1-nitrohexitols

Synthesis of Gold Glyconanoparticles and Biological Evaluation of Recombinant Gp120 Interactions

“…Preparation of the C -glycosides was accomplished upon reaction of the appropriate carbohydrate with nitromethane under basic conditions to provide cyclic derivatives favoring the β-pyranosylglycosides with the bulky nitromethyl group in the equatorial position. , Following an improved preparation method, C -(β- d -galactopyranosyl)- and C -(β- d -glucopyranosyl)nitromethanes ( 3 ) 20,21a,b and ( 4 ) 20,21c were obtained in yields of 50 and 53%, respectively . Hydrogenation over palladium/charcoal afforded C -(β- d -galactopyranosyl)- and C -(β- d -glucopyranosyl)methylamines ( 5 ) , and ( 6 ) , in virtually quantitative yields (Scheme )…”

“…15 was isolated as a colorless foam (80 mg, 0.11 mmol) in 90% yield after treating starting material 11 (100 mg, 0.25 mmol) following the procedure as for 14. 1 Preparation of Gold Glyconanoparticles: Gal-Au (17), Glc-Au (18), and Sp-Au (19). Following the procedure of Penades and co-workers, 15a a freshly prepared 12 mM solution of disulfide (14, 15, or 16) (0.12 mmol, 3 equiv disulfide or 6 equiv sulfide) in MeOH was added to a freshly prepared aqueous 25 mM solution of hydrogen tetrachloroaurate(III) hydrate (0.04 mmol, 1 equiv).…”

Amino sugars. LV. Absolute configuration of the carboxyethyl (lactyl) side chain of muramic acid[2-amino-3-0-(D-1-carboxyethyl)-2-deoxy-D-glucose]

“…Both L-glycero-L-galacto and L-glycero-L-talo configurations can be formed during the cyclization; the former configuration was selected on the basis of the earlier work of Sowden, Hough, and associates (see Sowden et al, 1962). Compound 13 was hydrogenated (Sowden and Oftedahl, 1961) into 1 -amino-2,6-anhydro-l ,7-dideoxy-L-g/ycero-L-ga/acto-heptitol ( 14), not previously described, and isolated as the crystalline tetraacetyl derivative 15. Treatment of 14 with sodium nitrite (Sowden and Oftedahl, 1961) afforded 2.6-anhydro-7-deoxy-L-g/ycero-L-ga/acto-heptitol ( 16) and 1,7dideoxy-L-mawio-heptulose ( 18), which could be separated by silica gel chromatography of the crystalline per-O-acetyl derivatives 1,3,4,5-tetra -Oacetyl -2,6 -anhydro -7 -deoxylg/ycero-L-gti/acto-heptitol (17) and 3,4,5-tri-O-acetyl-1.7-dideoxy-L-wo««o-heptulose (19), respectively.…”

“…Compound 13 was hydrogenated (Sowden and Oftedahl, 1961) into 1 -amino-2,6-anhydro-l ,7-dideoxy-L-g/ycero-L-ga/acto-heptitol ( 14), not previously described, and isolated as the crystalline tetraacetyl derivative 15. Treatment of 14 with sodium nitrite (Sowden and Oftedahl, 1961) afforded 2.6-anhydro-7-deoxy-L-g/ycero-L-ga/acto-heptitol ( 16) and 1,7dideoxy-L-mawio-heptulose ( 18), which could be separated by silica gel chromatography of the crystalline per-O-acetyl derivatives 1,3,4,5-tetra -Oacetyl -2,6 -anhydro -7 -deoxylg/ycero-L-gti/acto-heptitol (17) and 3,4,5-tri-O-acetyl-1.7-dideoxy-L-wo««o-heptulose (19), respectively. Assignment of structures to 17 and 19 was based on elementary analysis and nuclear magnetic resonance data.…”

“…We were able to show, however, that this compound is in fact 1,7-dideoxy-l -nitro-~-glycero-~-gal~ctoheptitol (10) by treatment with concentrated sulfuric acid (Nef, 1894) to give the known 7-deoxy-~-glycero-~-galactoheptose (12) (Jackson and Hudson, 1953). Heating of an aqueous solution of 10 (Sowden and Oftedahl, 1961) gave crystalline 2,6-anhydro-l,7-dideoxy-l-nitro-~-glycero-~-galacto-heptitol (13) in addition to a small proportion of Lrhamnose (9). Both L-glycero-L-galacfo and L-glycero-L-talo configurations can be formed during the cyclization; the former configuration was selected on the basis of the earlier work of Sowden, Hough, and associates (see Sowden et a/., 1962).…”