P-D-Mannofuranosides

Methyl 2,3 6,7-di-0-isopropylidene-p-D-a//o-heptopyranos-4-uloside, H-54 Methyl 2,3 4,5-di-0-isopropylidene-p-L-idoseptanoside, I-IO Methyl 2,3 5,6-di-0-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 2,3 5,6-di-0-isopropylidene-p-D-mannofuranoside, 1-71 Methyl (2,3 5,6-di-0-isopropylidenemannofuranosyl)acetate, M-174 Methyl 5-0-(2,3 5,6-di-0-isopropylidene-a-D-mannofuranosyl)-2,3-0-... 

Allyl 2,3 5,6-di-0-isopropylidene-a-D-mannofuranoside, 1-71 Allyl 2,3 5,6-di-O-isopropylidene-p-D-mannofuranoside, 1-71 Allyl 3,4,6-tri-0-benzyl-2 eoxy-2-C-methyl-a-D-mannopyranoside, D-307... 

It was found122 that 2,3 5,6-di-0-isopropylidene-D-mannose reacts with p-toluenesulfonyl chloride in pyridine, but the only product isolated was the corresponding mannofuranosylpyridinium p-toluenesulfonate. On the other hand, when 2 moles of the sodium salt of 2,3 5,6-di-0-iso-propylidene-D-mannose, dissolved in dry petroleum ether, were treated with one mole of p-toluenesulfonyl chloride, there apparently resulted the nonreducing-disaccharide derivative, 2,3 5,6-di-0-isopropylidene-D-mannofuranosyl 2,3 5,6-di-0-isopropylidene-D-mannofuranoside (a compound later prepared121 by condensation of 2,3 5,6-di-0-isopropylidene-D-mannosyl chloride with 2,3 5,6-di-0-isopropylidene-D-mannose). Presumably, the following reactions had taken place (Ip = isopropylidene) ... 

P. Koll, A. Fortsch, and J. Kopf, Methyl-2,6-anhydro-a-D-mannofuranosid. Eine verbesserte Darstellungsmethode sowie die Bestimmung der Kristall- und Molekulstruktur, J. Carbohydr. Chem., 2 (1983) 189-200. 

P. Koll and H. Komander, Methyl-2,6-anhydro-a-D-mannofuranosid, ein Nebenprodukt der Methanolyse von Methyl-2,6-anhydro-a-D-mannopyranosid, Liebigs Ann. Chem., (1981) 1960-1966. 

If p-toluenesulfonylation occurred under these conditions, the product distribution would depend on [R X]. Changing the concentration of p-toluenesulfonyl chloride from 0.10 M to 1.2 M did not affect the product ratio in a reaction with a dialkylstannylene acetal of methyl 2,3-0-isopropylidene-D-mannofuranoside. This result provides additional evidence that this reaction and all slower reactions occur under conditions where equilibration is faster than reaction. 

Fleet, G W J, Fellows, L E, Smith, P W, Synthesis of deoxymannojirimycin, fagomine, deoxynoj irimycin, 2-acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol, 2-acetamido-1,5-imino-1,2, 5-trideoxy-D-glucitol, 25,3R,4R,5R-trihydroxypipecolic acid and 25,3R,4R,55-trihydrox3fpipecolic acid from methyl 3-0-benzyl-2,5-dideoxy-2,6-imino-a-D-mannofuranoside, Tetrahedron, 43, 979-990, 1987. 

Diethyl azodicarboxylate and triphenylphosphine permit the condensation between aldose derivatives with a free reducing centre and phenols. 2,3 5,6-Di-0-isopropylidene-D-mannose gave 67% of the phenyl o-D-mannofuranoside derivative and 16% of the /3-anomer, while 2,3 4,6-di-O-cyclohexylidene-a-D-mannose afforded access to p-nitrophenyl /3-D-mannopyranoside in 58% yield and other, substituted aryl analogues. Unsubstituted sugars can be subjected to the procedure, D-glucose giving mainly the phenyl 3-pyranoside. ... 

Benzyl 3,4-0-isopropylidene-a-D-ajabinopyranoside, B-14 Benzyl 3,4-0-isopropylidene-p-L-arabinopyranoside, B-14 Benzyl 2,3-0-isopropylidene-5,6-di-O-mesyl-a-D-mannofuranoside, B-19 Benzyl 3,4-0-isopropylidene-p-D-galactopyranoside, B-15 Benzyl 4,6-0-isopropylidene-p-D-galactopyranoside, B-15 Benzyl 2,3-0-isopropylidene-5-0-(2,3-0-isopropylidene-p-D-ribofuranosyl)-p-D-ribofuranoside, R-121... 

Benzyl 2,3-0-isopropylidene-a-D-lyxofuranoside, 1-70 Benzyl 2,3-0-isopropylidene-p-D-lyxofuranoside, L-72 Benzyl 2,3-0-isopropylidene-a-D-mannofuranoside, B-19 Benzyl 2,3-0-isopropylidene-a-D-mannopyranoside, B-19 Benzyl 2,3-0-isopropylidene-5-0-mesyl-a-D-lyxofuranoside, 1-70 Benzyl 2,3-0-isopropylidene-6-0-mesyl-a-D-mannofuranoside, B-19 Benzyl 2,3-0-isopropylidene-4-0-mesyl-a-L-rhamnopyranoside, B-20 Benzyl 3,4-0-isopropylidene-2-C-methyl-p-L-arabinopyranoside, M-229 Benzyl 3,4-0-isopropylidene-2-C-methyl-p-L-ribopyranoside, M-286 Benzyl 3,4-0-isopropylidene-2-0-methyl-p-D-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-2-0-methyl-p-L-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-p-D- /7// ro-pentopyranosid-2-ulose, P-42 Benzyl 2,3-0-isopropylidene-a-L-rhamnopyranoside, B-20 Benzyl 2,3-0-isopropylidene-p-D-ribofuranuronoside, R-146 Benzyl 3,4-0-isopropylidene-p-D-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-p-L-ribopyranoside, B-21 Benzyl 3,4-0-isopropylidene-2-0-(2,3,4,6-tetra-0-acetyl-p-D-glucopyranosyl)-p-D-arabinopyranoside, G-284 Benzyl 2,3-0-isopropylidene-5-0-(2,3,4,6-tetra-0-acetyl-p-D-glucopyranosyl)-p-D-ribofuranoside, G-462 Benzyl 3,4-0-isopropylidene-2-0-tosyl-a-D-arabinopyranoside, B-14 Benzyl 3,4-0-isopropylidene-2-tosyl-p-L-arabinopyranoside, B-14 Benzyl 3,4-0-isopropylidene-2-0-(2,3,5-tri-0-benzoyl-a-L-arabinofuranosyl)-p-L-arabinopyranoside, A-801 Benzyl 3,4-0-isopropylidene-6-0-trityl-p-D-galactopyranoside, B-15... 

Di- O -isopropylidene- p-D-idofuranose, 1-69 1,2 3,5-Di- O -isopropylidene- p-L-idofuranose, 1-69 1,2 5,6-Di- O -isopropylidene- p-L-idofuranose, 1-69 1,2 3,4-Di- O -isopropylidene- p-L-idoseptanose, I-10 1,2 4,5-Di- O -isopropylidene- p-L-idoseptanose, I-10 1,2 5,6-Di- O -isopropy lidene-L-c/ >o -inositol, 1-28 l,2 4,5-Di-0-isopropylidene-mMco-inositol, 1-31 1,2 3,4-Di- O -isopropy lidene-myo -inositol, 1-32 1,2 4,5-Di- O -isopropy lidene-myo -inositol, 1-32 1,2 5,6-Di- O -isopropy lidene-myo -inositol, 1-32 l,2 3,4-Di-0-isopropylidene-D-mannitol, M-25 l,2 3,6-Di-0-isopropylidene-D-mannitol, M-25 l,2 4,5-Di-0-isopropylidene-D-mannitol, M-25 l,2 4,6-Di-0-isopropylidene-D-mannitol, M-25 l,2 5,6-Di-0-isopropylidene-D-mannitol, M-25 2,3 4,5-Di-0-isopropylidene-D-mannitol, M-25 2,4 3,5-Di-0-isopropylidene-D-mannitol, M-25 l,2 5,6-Di-0-isopropylidene-L-mannitol, M-25 2,3 5,6-Di-0-isopropylidene-a-D-mannofuranose, 1-71 2,3 5,6-Di-0-isopropylidene-a-L-niannofiiranose, 1-71 2,3 5,6-Di-(9-isopropylidene-a-D-niannofuranosyl bromide, M-26 2,3 5,6-Di-O-isopropylidene-a-D-mannofuranosyl chloride, M-27 2,3 5,6-Di-O-isopropylidene-p-D-mannofuranosyl chloride, M-27 2,3 5,6-Di-O-isopropylidene-a-D-mannofuranosyl 2,3 5,6-di-0-isopropylidene-a-D-mannofuranoside, M-30 2,3 5,6-Di-O-isopropylidene-p-D-mannofuranosyl 2,3 5,6-di-0-isopropylidene-a-D-mannofuranoside, M-31 2,3 5,6-Di-0-isopropylidene-a-D-mannofuranosyl iodide, M-29 2,3 5,6-Di-0-isopropylidene-p-D-mannofuranosyl 2,3,5,6-tetra-O-acetyl-a-D-mannofuranoside, M-31... 

Methyl 2-0-benzyl-3,4-0-isopropylidene-p-L-arabinopyranoside, M-197 Methyl 2-0-benzyl-3,4-O-isopropylidene-a-L-fucopyranoside, M-198 Methyl 3- 0 -benzyl-1,2- O -isopropylidene- p-L-idofuranuronate, 1-12 Methyl 5-0-benzyl-2,3-0-isopropylidene-a-D-lyxofuranoside, 1-70 Methyl 5-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 6-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 4-O-benzyl-2,3-O-isopropylidene-a-L-rhamnopyranoside, M-207 Methyl 2-O-benzyl-3,5-O-isopropylidene-a-D-xylofuranoside, M-216 Methyl 2-O-benzyl-3,5-O-isopropylidene-p-D-xylofuranoside, M-216 Methyl 3-0-benzyl-2-0-methyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-2-0-methyl-a-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 5-0-benzyl-2-0-methyl-p-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 2,6-0-benzyl-3-0-methyl-a-D-mannopyranoside, M-271 Methyl 3-0-benzyl-2-O-methyl-6-0-tosyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-3-0-methyl-a-D-xylofuranoside, M-216 Methyl 3-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 4-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 3-0-benzyl-p-L-ribofuranoside, M-208 Methyl 3-O-benzyl-4-O -(2,3,4-tri-O-benzyl-p-D-xylopyranosyl)-p-D-xylopyranoside, X-80... 

Methyl 2,3-di-O-benzyl-5,6-0-isopropylidene-a-D-galactofuranoside, M-184 Methyl 2,3-di-O-benzyl-5,6-0-isopropylidene-p-D-galactofuranoside, M-184 Methyl 2,6-di-O-benzyl-a-D-mannofuranoside, M-203 Methyl 2,3-di-0-benzyl-a-D-mannopyranoside, M-204 Methyl 3,6-di-O-benzyl-a-D-mannopyranoside, M-204 Methyl 2,3-di- O -benzyl-5- O -niesyl-6-0 -trityl- p-D-glucofuranoside, M-189 Methyl 2,4-di-O-benzyl-3-0-methyl-a-L-fucopyranoside, M-183 Methyl 3,4-di-0-benzyl-2-0-methyl-a-L-fucopyranoside, M-183 Methyl 3,4-di-0-benzyl-2-0-methyl-a-D-rhamnopyranoside, M-207 Methyl 3,4-di-O-benzyl-a-D-rhamnopyranoside, M-207 Methyl 2,3-di-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 2,4-di-O-benzyl-a-L-rhamnopyranoside, M-207 Methyl 3,4-di-O-benzyl-a-L-rhanmopyranoside, M-207 Methyl 3,5-di-0-benzyl-a-D-ribofnranoside, M-208 Methyl 2,3-di-0-benzyl-6-0-tosyl-a-D-altropyranoside, M-149 Methyl 2,3-di-O-benzyl-6-O-tosyl-p-D-galactofuranoside, M-184 Methyl 2,4-di-0-benzyl-3-0-(2,3,4-tri-0-acetyl-a-L-rhanmopyranosyl)-a-D-xylopyranoside, R-77... 

Methyl 6-0-acetyl-2,3-di-O-benzyl-a-D-mannopyranoside, M-204 Methyl 4-0-acetyl-2,3-di-0-methyl-a-D-mannopyranoside, D-748 Methyl 4-0-acetyl-2,3-0-isopropylidene-6-0-methyl-a-D-mannopyranoside, M-200 Methyl 4-O-acetyl-a-D-mannopyranoside, M-204 Methyl 6-O-acetyl-p-D-mannopyranoside, M-205 Methyl 4-0-acetyl-6-0-methyl-a-D-mannopyranoside, M-274 Methyl 2-0-acetyl-3,4,6-tri-0-benzyl-a-D-mannopyranoside, M-204 Methyl 4-0-acetyl-2,3,6-tri-0-methyl-a-D-mannopyranoside, T-190 Methyl 3-amino-3-deoxy-p-D-mannopyranoside, A-313 Methyl 3-amino-3-deoxy-a-D-mannopyranoside, A-313 Methyl 2,3-anhydro-4,6-0-benzylidene-(3-D-mannopyranoside, M-169 Methyl 2,3-anhydro-4,6-0-benzylidene-a-D-mannopyranoside, A-676 Methyl 2,3-anhydro-4-0-benzyl-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2,3-anhydro-4,6-di-0-methyl-p-D-mannopyranoside, A-676 Methyl 2,3-anhydro-4,6-di-0-tosyl-a-D-mannopyranoside, A-676 Methyl 2,3-anhydro-4,6-0-ethylidene- -D-mannopyranoside, A-676 Methyl 2,6-anhydro-a-D-mannofuranoside, A-671 Methyl 3,6-anhydro-a-D-mannofuranoside, A-679 Methyl 2,3-anhydro-a-D-mannopyranoside, 8CI, A-676 Methyl 2,3-anhydro-p-D-mannopyranoside, A-676 Methyl 2,6-anhydro-a-D-mannopyranoside, A-678 Methyl 3,6-anhydro-a-D-mannopyranoside, A-679 Methyl 3,6-anhydro-p-D-mannopyranoside, A-679 Methyl 2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 6-azido-6-deoxy-2,3-0 -isopropylidene-a-D-mannofuranoside, A-913... 

Methyl 2,3-diacetainido-2,3-dideoxy-a-D-mannopyranoside, D-449 Methyl 2,3-diacetamido-2,3-dideoxy-p-D-mannopyranoside, D-449 Methyl 3,6-diacetamido-3,6-dideoxy-a-D-mannopyranoside, D-451 Methyl 3,4-di-0-acetyl-2,6-anhydro-a-D-niannopyranoside, A-67S Methyl 3,4-di-0-acetyl-2,6-anhydro-p-i>mannopyranoside, A-67S Methyl 2,3-di-0-acetyl-4,6-0-benzylidene-a-D-mannopyranoside, M-169 Methyl 2,4-di-0-acetyl-3,6-di-0-benzoyl-a-D-mannopyranoside, M-204 Methyl 4,6-di-0-acetyl-2,3-di-0-benzyl-a-D-mannopyranoside, M-204 Methyl 2,3-di-0-acetyl-4,6-0-ethylidene-a-D-mannopyranoside, M-I80 Methyl 5,6-di-0-acetyl-2,3-0-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 4,6-di-O-acetyl-a-D-mannopyranoside, M-204 Methyl 2,3-di-0-acetyl-4,6-0-methylene-a-D-mannopyranoside, M-204 Methyl 2,3-diamino-2,3-dideoxy-p-D-mannopyranoside, D-449 Methyl 3,6-diamino-3,6-dideoxy-a-D-mannopyranoside, D-451 Methyl 3,6-di-0-benzoyl-2,4-di-0-methyl-a-D-mannopyranoside, D-749 Methyl 3,6-di-O-benzoyl-a-D-mannopyranoside, M-204 Methyl 2,6-di-0-benzoyl-3-0-methyl-p-D-mannopyranoside, M-205 Methyl 2,3-di-0-benzyl-4,6-0-benzylidene-a-D-mannopyranoside, M-169 Methyl 2,3 4,6-di-0-benzylidenemannopyranoside 0L-i>-( R, R)-form, M-172... 

Methyl 2,6-di-O-benzyl-a-D-mannofuranoside, M-203 Methyl 2,3-di-O-benzyl-a-D-maimopyranoside, M-204 Methyl 3,6-di-O-benzyl-a-D-maimopyranoside, M-204 Methyl 2,3 4,6-di-0-ethylidene-a-i>mannopyraiioside, M-180 Methyl 2,3 4,6-di-0-ethylidene-p-i>maimopyraiioside, M-180 Methyl 2,3 5,6-di-0-isopropylidene-a-D-maimofiiraiioside, I-7I Methyl 2,3 5,6-di-0-isopropylidene-p-D-maimofiiraiioside, I-7I Methyl 2,3 4,6-di-0-isopropylidene-a-D-maimopyranoside, M-200 Methyl 2,3-di-0-isopropylidene-5-0-methyl-a-i>majinofuranoside, 1-71... 

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