D-Mannose derivatives

D-mannose derivatives. Chitose and its oxidation products must then necessarily have a D-glucose configuration. The problem thus presented was solved by Levene and LaForge in 191554- 58 in the following manner. 

Di(2,3,4,6-tetra-0-acetyl-b-D-mannopyranosyl)-l,2,5-oxadiazole 2-oxide has been synthesized from D-mannose by a route, involving as the key step, dimerization of mannopyranosyl nitrile oxide. Three methods have been used for the generation of the nitrile oxide isocyanate-mediated dehydration of nitro-methylmannose derivative, treatment of aldoxime with aqueous hypochlorite and base-induced dehydrochlorination of hydroximoyl chloride. D-gluco, D-galacto, D-xylo and L-fucopyranosyl analogs has been prepared similarly. The structure of D-mannose-derived 1,2,5-oxadiazole 2-oxide has been established by X-ray crystallography (478). 

Glycosylation of Trichloroacetimidates of 2-Azido-2-deoxy-D-mannose Derivatives... 

Oligosaccharid-Derivate beobachtet v.i27,27l) ebenso bei der Einwirkung von Titan(IV)-bromid 89,276) Jn Mannose-Derivate ist die Reaktion nicht moglich 278)... 

C. Nobrega and J. T. Vazquez, Conformational study of the hydroxymethyl group in a-D-mannose derivatives, Tetrahedron Asymmetry, 14 (2003) 2793-2801. 

T. Uryu, K. Hatanaka, Y. Sakomoto, K. Harima, A. Hagino, K. Ito, A. Funamoto, and K. Matsuzaki, Synthesis of substituted polysaccharides by ring-opening polymerization of 1,6-anhydro-D-glucose and 1,6-anhydro-D-mannose derivatives, Nippon Kagaku Kaishi, (1982) 1638-1644. 

J. Dolezalova, T. Trnka, and M. Cerny, Preparation of 1,6 3,4-dianhydro-/i-n-altropyranose as starting substance for the synthesis of 3-substituted D-mannose derivatives, Collect. Czech. Chem. Commun., 47 (1982) 2415-2422. 

When triacetyl-n-glucal is treated with perbenzoic acid in ethyl acetate and water, some D-glucose derivatives are produced in detectable amounts in addition to the predominant D-mannose derivatives. 

A most promising development is the observation that dibutylstannylene acetals of L-rhamnose and D-mannose derivatives having 0-1 and 0-2 unprotected react with primary and secondary triflates of sugars under mild conditions to give in good yields cis-(l— 2)-linked disaccharides with inversion in the glycosyl acceptor (see Fig. 57).230 As noted in Table X, L-rhamnose derivatives give better yields than shown for the mannose derivatives in Fig. 57. 

Zhang, D, Sueling, C, Miller, M J, The hetero Diels-Alder reactions between D-mannose-derived halonitroso compounds and cyclopentadiene scope and limitations, J. Org. Chem., 63, 885-888,1998. 

In 1982, Vasella and Voeffray [196] presented a synthesis of (+)-nojirimycin (5-amino-5-deoxy-D-glucose) using the 1,3-dipolar cycloaddition of a d-mannose-derived nitrone to furan. The chiral source in that synthesis (d-mannose) is not recovered. Jager and Muller used... 

Treatment of the 2-OTs D-mannose derivative 27 with a base affords the 1,2-anhydro-glucose derivative 28, while a similar reaction of the 2-OTs glucopyranose 29 yields the 1,2-anhydro-D-mannopyranose 30. 

Two examples of desulfurization reactions of sugar dithioacetals, in which episulfonium ion formation is postulated, are pertinent here. Treatment of the 3-amino-3,6-dideoxy-D-mannose derivative (324) with Raney nickel gave some of the 1,2,6-trideoxy alditol (326), along with the... 

Anhydrides of pyranoses and furanoses are usually formed by intramolecular displacements of 6-sulfonyloxy groups.370-394 These replacements often occur very readily (for example, during methyla-tion,24 and during attempted solvolysis of 3-0-acetyl-l,2-0-isopropyli-dene-5,6-di-0-p-tolylsulfonyl-a-D-glucofuranose280). 3,6-Anhydro rings have been introduced into amylose chains,68-395 and 2-amino-3,6-anhydro-2-deoxy-D-mannose derivatives have been prepared.396... 

D-mannose derivatives.437 All such reactions that they examined with sulfonates of methyl 6-deoxy-2,3-0-isopropylidene-a-D-manno-pyranoside (175) resulted in the formation of furanoside products, and this result probably accounts for some of the conflicting accounts of desulfonylation of the L enantiomorph of 175 (R = Ts).322,438 With acetate ion in boiling N,N-dimethylformamide, the methanesulfonate (175, R = Ms) gave, after saponification, a 65% yield of a mixture of methyl 6-deoxy-2-3-0-isopropylidene-a-D-talofuranoside (176, R = OH) with methyl 6-deoxy-2-3-0-isopropylidene-/3-L-allofurano-side (177, R = OH) in the ratio of 7 1. Displacements atC-5 of the sul-fonylated furanose derivatives 176 and 177 (R = OMs,OTs, or OBs)... 

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