First Stereqselective Synthesis of Nitrophenyl 2-Deoxy- β-D-glycosides
Titel:
First Stereqselective Synthesis of Nitrophenyl 2-Deoxy- β-D-glycosides
Auteur:
Bielauska, Halszka Michalska, Maria
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 5 (1986) nr. 3 pagina's 445-458
Jaar:
1986-09-01
Inhoud:
α-Dithiophosphates of peracetylated 2-deoxyhexc-pyranoses, 1a, 1b and 2, uhich are easily prepared by addition of organic phosphorodithioic acids to glycais react smoothly with resin-bound 2- and 4-nitrophenoxides to give stereoselectively the respective nitrophenyl 2-deoxy-β-D-hexopyranosides (3, 4, 5 and 6) in high yields. Glycosylation of the 2, 4-dinitro'phenoxide, however, leads with comparable stereoselectivity to 2,4-dinitrophenyl 2-deoxy- α-D-hexopyranosides (7 and 8). Glycosides 3 - 6 are quantitatively deacetylatec by Amberlyst A-26 (OH-), whereas glycosides 7 and 8, under the same reaction conditions undergo splitting of the O-glycosidic bond.
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