A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids Full article
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Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Output data | Year: 2000, Volume: 49, Number: 7, Pages: 1305-1309 Pages count : 5 DOI: 10.1007/bf02495780 | ||
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Abstract:
A novel approach to the functionalization of aglycon in allyl glycosides is described. The method comprises ozonolysis of the double bond in the allyl group, leading to the corresponding aldehyde, and subsequent transformation of the latter into the corresponding oxime, which is finally reduced to give the amine. The efficiency of this synthetic sequence (yield ∼90%) is exemplified by the transformation of two allyl lactoside derivatives into selectively protected 2-aminoethyl lactosides. The latter are convenient common building blocks for the synthesis of carbohydrate chains of glycolipids that have a lactose unit at the reducing end.
Cite:
Kononov L.O.
, Cheshev P.E.
, Nifant'ev N.E.
A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids
Russian Chemical Bulletin. 2000. V.49. N7. P.1305-1309. DOI: 10.1007/bf02495780 WOS Scopus OpenAlex
A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids
Russian Chemical Bulletin. 2000. V.49. N7. P.1305-1309. DOI: 10.1007/bf02495780 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000089679100026 |
| Scopus: | 2-s2.0-0034336776 |
| OpenAlex: | W2951015260 |