Allose 2-amino-2-deoxy

Aldotriouronic acids, 73 Alginic acid, fractionation, 55 L-guluronic acid in, 88 Alkaloids, biosynthesis of, 269 Allose, 2-amino-2-deoxy-n-, derivatives of, 191... 

Alginic acid, 279, 281, 286, 314, 322 esters of, 279, 314 salts of, 275, 279, 280, 286 Allopyranoside, methyl 2-acetamido-2-deoxy-a-D-, 3-methyl ethers, 202 Allose, 2-amino-2-deoxy-D-, methyl ethers of, 202, 214... 

Mycarose Mycinose Neuraminic acid (Neu) 2,6-D ideoxy-3- C-methy I-l- ribo- hexose 6-Deoxy-2,3-di-Omethyl-D-allose 5-Amino-3,5-dideoxy-D-g/ycero-D-ga/acfo-non-2-ulosonic acid... 

Nevertheless, compound 81 was definitely obtained later by deamination of 2-amino-l,6-anhydro-2-deoxy-j6-D-mannopyranose (103) with nitrous acid, and was identified by reduction to 2,5-anhydro-D-glucitol.366 An analogous deamination was performed with 2-amino-l,6-anhydro-2-deoxy-3-0-tosyl-/l-D-altropyranose to give, after detosylation, 2,5-anhydro-D-allose.361... 

Subsequently Jeanloz31 was able to convert 2-amino-2-deoxy-D-glucose into 2-amino-2-deoxy-D-allose (VI) by solvolysis of the 3-methylsulfonyl ester of methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-a-D-glucopyrano-side (V). 

Methyl ethers of 2-amino-2-deoxy-D-allose have been prepared in order to be subsequently degraded into methyl ethers of n-ribose. Methylation of methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-o -D-alloside gave the 3-methyl ether, which, in turn, was hydrolyzed to afford methyl 2-acetamido-2-deoxy-3-0-methyl-a-D-allopyranoside. After partial methylation, a dimethyl ether, probably the 3,6, was isolated, whereas exhaustive methylation afforded the 3,4,6-trimethyl ether. An identical trimethyl ether was isolated after methylation of methyl 2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-a-n-alloside. Hydrolysis of the methyl glycosides of both the 3-methyl and the 3,4,6-trimethyl ethers gave crystalline hydrochlorides, and the base of the former ether was characterized by means of its crystalline Schiff base with 2-hydroxynaphthaldehyde. 

W. Meyer zu Reckendorf, Transformation of 2-amino-2-deoxy-D-glucose into an aziridine derivative of 2-amino-2-deoxy-D-allose, Chem. Ber., 97 (1964) 325-330. 

W. Rhoads and P. H. Gross, Epimino and oxazolino derivatives of 2-amino-2-deoxy-D-allose, Carbohydr. Res, 11 (1969) 561-564. 

W. Meyer zu Reckendorf and W. A. Boimer, Sulfur substitution products of amino sugars. VI. Synthesis of 2-amino-2-deoxy-3-thio-D-allose derivatives through thiazoline intermediates. Tetrahedron, 19 (1963) 1721-1725. 

From Chiral Non-carbohydrates - A section on amino-sugars has been included in a review of the synthesis of monosaccharides from non-carbohydrate sources. L-Ristosamine 42 was synthesized by addition of the Cs-synthon 40 (which contains a masked aldehyde function that can be readily demasked by mild acid hydrolysis) to the L-lactaldehyde derivative 41 (Scheme 11). The TBSOP adduct 43 (Vol.27, p.ll4), derived from 2,3-< -isopropylidene-D-glycer-aldehyde, has been converted into 3-amino-3-deoxy-D-altrose 46 by a route involving cis-hydroxylation of its unsaturated lactam moiety and periodate cleavage between C-6 and C-7 of the derived heptitol derivative 45 as key steps (Scheme 12). 3-Amino-3-deoxy-L-allose was obtained by converting 43 to its C-3... 

Racemic 3-amino-sugars have been synthesized through hetero-Diels-Alder reactions of enaminones, Thus the major adduct from enamlnone (M6) and ethyl vinyl ether was converted to the M-deoxy-rlstosamlnide (M ) (Scheme 19). Racemic 5,6-dideoxy-5-amlno-allose derivatives such as (M8) have been constructed from the hetero-Dlels-Alder adducts of diene (M9) with acylnitroso... 

O -p-D-Xylopyranosyl-D-allose, X-20 6-0-p-D-Xylopyranosyl-2-amino-2-deoxy-D-glucose, X-21 a-D-Xylopyranosyl-(l 3)-a-L-arabinofuranosyl-(l ->3)-L-arabinose, X-22 p-D-Xylopyranosyl-(l ->3)-a-L-arabinofuranosyl-(l ->3)-L-arabinose, X-23 p-D-Xylopyranosyl-(l ->5)-a-L-arabinofuranosyl-(l ->3)-L-arabinose, X-24 p-D-Xylopyranosyl-(l ->5)-a-L-arabinofuranosyl-(l ->5)-L-arabinose, X-25 p-D-Xylopyranosyl-(l ->3)-a-L-arabinopyranosyl-(l ->4)-[p-D-apiofuraiiosyl-... 

From Achiral Non-carbohydrates. — 3-Deoxy-3-guanidino-D-threose 48 equilibrates with 49. a transition state inhibitor for galactosidase. It was synthesized as shown in Scheme 12 from epoxide 47, which was obtained by porcine pancreatic lipase catalysed enantioselective esterification of the racemic epoxy-alcohol precursor. 6-Deoxy-L-talonolactone 50 was synthesized by an asymmetric aldol condensation - dihydroxylation sequence (Vol.24, p.lS2) in improved diastereoselectivity and was converted into 2-acetamido-2,6-dideoxy-L-fucose (shown as its furanose isomer 51 in Scheme 13), 3-acetamido-3,6Hlideoxy-L-idose and 5-acetamido-S,6-dideoxy-D-allose by S 2 displacements of triflate with azide ion. 4-Amino-4-deoxy-DL-erthrose 53 was obtained from the hetero-Diels-Alder adduct 52 by a sequence of reactions including cis-dihydroxylation (OSO4, NMNO) of the alkene moiety (Scheme 14). The synthesis of a racemic branched-chain lactam is covered in Chapter 16. 

Amino-2,6-dideoxy-D-allose and -altrose hydrochlorides have been prepared by application of the Kuhn modification of the cyanohydrin synthesis to 5-deoxy-D-ribose, the overall yields of the two amino-sugars being roughly the same as those obtained using the nitromethane synthesis. ... 

Investigation of the biosynthesis of polyoxin antibiotics from labelled substrates by S. cacaoi has revealed that the 5-amino-5-deoxy-)3-D-allofuranosyl-uronic acid residue of these antibiotics is not derived via oxidation of either D-glucose or o-allose at C-6, but is formed from triose precursors. ... 

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