Article

The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions.

Laboratoire de Chimie Organique II, C.N.R.S., Université de Lyon I, Villeurbanne, France.
Carbohydrate Research (impact factor: 2.33). 08/1990; 202:151-64. DOI:10.1016/0008-6215(90)84077-8 pp.151-64
Source: PubMed

ABSTRACT 1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-beta-D-glu copyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-alpha-D-glucopyra nosyl bromides have been used as donors in glycosylation reactions with model alcohols. beta-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.

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Keywords

1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-beta-D-glu copyranoses
 
3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-alpha-D-glucopyra nosyl bromides
 
alcohols
 
glucopyranosyl bromides
 
glycosylation reactions
 
low reactivity
 
main product
 
model alcohols
 
strong participation