0-D-Mannopyranose, 4-

Fig. 9. Partial structural formulas and shorthand notations for principal hemiceUuloses found in wood, where the sugar units ate noted as P-D-xylopyranose (Xylp), 4-Omethyl-a-D-glucopyranosyluronic acid (GlupU), a-L-arabinofuranose (Araf), P-D-glucopyranose (Glup), P-D-mannopyranose (Manp), and P-D-galactopyranose (Galp) for (a) arabino-4-O-methylglucuronoxylan from softwood, (b) 0-acetyl-galactoglucomannan from softwood, and...

The specific optical rotations of pure a- and p-D-mannopyranose are -1-29.3° and -17.0°, respectively. When either form is dissolved in water, mutarotation occurs, and the observed rotation of the solution changes until a final rotation of -1-14.2° is observed. Assuming that only a- and p-pyranose forms are present, calculate the percent of each isomer at equilibrium. 

Table IV. Comparison of Anomeric Proton (Hi) Chemical Shifts for Free and Acetylated D-gluco and D-mannopyranoses With Those of Related 2-Deoxy Sugar Derivatives. Effect of Replacing an Axial or an Equatorial C2-Methylene Proton With a Hydroxy or Actetoxy Substituent...

Problem 25,13 Draw /3-o-galactopyranose and jS-D-mannopyranose in their more stable chair conformations. Label each ring substituent as either axial or equatorial. Which would you expect to be more stable, galactose or mannose ... 

I4l6-Tii-0-benzoyl-[(S)-1,2-0-chloro(methoxy)methylene]-p-D-mannopyranose... 

Carba-a-D-galactopyranose (7) has also been synthesized from quebrachi-tol, by Paulsen and coworkers,as well as carba- -D-mannopyranose (114). 

As 2-amino-2-deoxy-D-mannose is tumorstatic and 2-acetamido-2-deoxy-D-mannose 6-phosphate is an obligatory intermediate in the biosynthetic pathway to sialic acid, displacement of the essential OH-6 with a fluorine atom should be interesting from the biological viewpoint. 2-Acetamido-1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-D-mannopyranose (see Table 111 in Section 11,3) and its O- and A,0-deacetyl derivatives were prepared the first compound showed weak anticancer activity. 

A-Acetyl-9-deoxy-9-fluoroneuraminic acid (591) was prepared by treatment of a protected 6-hydroxyl precursor with A, A-diethylaminosulfur trifluoride (DAST) or through condensation of 2-acetamido-2,6-dideoxy-6-fluoro-D-mannopyranose with potassium di(/ >r/-butyl) oxaloacetate. Compound 591 is a substrate for cytidine monophosphate (CMP)-sialic acid synthetase, giving rise to CMP-5-A-acetyl-9-deoxy-9-fluoroneuraminic acid, which is cytotoxic against tumor cells. 5-A-Acetyl-3-fluoroneuraminic acids 592-594 were prepared through fluorine (or acetyl hypofluorite) addition (in AcOH) to methyl 5-acetamido-4,7,8,9-tetra-0-acetyI-2,6-anhy-dro-2,3,5-trideoxy-D- /ycm>D- a/arto-non-2-enopyranosate. Compound 592 was found to be a potent neuraminidase inhibitor. 

Acetamido-2-deoxy-D-galactopyranose (—), and 2-Acetamido-2-deoxy-D-mannopyranose ( ) at Anomeric Equilibrium in Aqueous Solution (redrawn from Ref. 28), and 2-Acetamido-2-deoxy-D-glucopyranose (- -) at Anomeric Equilibrium in Aqueous Solution. (Redrawn from Ref. 29.)... 

Support for this result was obtained from the taste of 1,5-anhydrohexitols, which, only for purposes of comparison, can be regarded as 1-deoxyal-dopyranoses. 1,5-Anhydro-D-glucitol (that is, the incorrectly named 1-deoxy-D-glucopyranose ) (14), 1,5-anhydro-D-mannitol ( 1-deoxy-D-mannopyranose or 2-deoxy-D-fructopyranose ) (15), and 1,5-anhydro-D-galactitol ( l-deoxy-o-galactopyranose ) (16) are all purely sweet, without any trace of bitterness. Furthermore, the complete absence of bitterness of 1,5-anhydromannitol (16) clearly indicates that the anomeric... 

C-5, C-3, C-2, C-4, and C-6 of a-D-mannopyranose. There is very little / -D-mannopyranose present. Peaks 14,15,16,19, and 24 (see Fig. 4) can readily be assigned to a-D-glucopyranose. These results corroborated the findings by other researchers as to the types of carbohydrates present in glucoamylase.104... 

C8H15N0aH20 2-Acetamido-2-deoxy- -D—mannopyranose, monohydrate NACMAN10 34 355... 

It was found possible to saponify ovomucoid with sodium hydroxide and to methylate simultaneously with methyl Bulfate, the carbohydrate residue thereby forming an N-acetyl methyl derivative.14 Hydrolysis of this material yielded N-acetyl-3,4,6-trimethyl-D-glucosamine (7 moles) (LIVJ, D-mannopyranose (2 moles) (LV), 3,4,6-trimethyl-D-mannopy-ranose (1 mole) (LVI), and tetramethyl-D-galactopyranose (1 mole) (LVII). 

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