The chromous chloride promoted addition of N-chlorocarbamates to enol ethers the synthesis of N-alkoxycarbonyl derivatives of 2-amino sugars and of α-amino ketones and aldehydes

1970 ◽  
Vol 11 (56) ◽  
pp. 4887-4890 ◽  
Author(s):  
J. Lessard ◽  
H. Driguez ◽  
J.P. Vermes
Keyword(s):  
Amino Sugars ◽  
Enol Ethers ◽  
Derivatives Of ◽  
Chromous Chloride

The chromous chloride promoted addition of N-haloamides to olefins. V. The addition of N-chloroamides to enol ethers: synthesis of acyloxy and acyl derivatives of α-amino acetals and ketals (aldehydes and ketones) and of 2-amino sugars

1978 ◽  
Vol 56 (1) ◽  
pp. 119-130 ◽  
Author(s):  
Hugues Driguez ◽  
Jean-Paul Vermes ◽  
Jean Lessard
Keyword(s):  
Addition Product ◽  
Amino Sugars ◽  
Enol Ethers ◽  
Aldehydes And Ketones ◽  
Work Up ◽  
Derivatives Of ◽  
Chromous Chloride ◽  
Acyl Derivatives

The chromous chloride promoted addition of N-chlorocarbamates and N-chlorocarboxamides to 1-methoxycyclohexene, ethoxyethylene, dihydropyran, and (1-methoxyethylidene)-cyclohexane gave, in 60 to 85% yields, either α-acyloxy- or α-acylamino ketals and acetals, or the corresponding ketones and aldehydes depending on the work-up conditions. The regio-specificity of the addition was higher with the first two enol ethers (≥97%) than with the latter two (≥85%). N-Chlorourethane was added to 17-methoxymethylenandrost-4-en-3-one (19) and the sole addition product isolated was the 17α-chloro-20-ethoxycarbonylamino derivative 20 in 75% yield. Additions to triacetyl-D-glucal and 3-O-acetyl-4,6-O-benzylidene-D-glucal followed by solvolysis under Koenigs–Knorr conditions led predominantly to 2-amino-gluco-pyranosides in 30 to 65% yields, whereas additions to 3-O-acetyl-4,6-O-benzylidene-D-allal gave 2-amino altropyranosides in 40 to 56% yields.

Amino sugars. XXVII. The synthesis of derivatives of 3-amino-3,4,6-trideoxy-D- or L-xylo-hexopyranose

1972 ◽  
Vol 37 (9) ◽  
pp. 2985-2993 ◽  
Author(s):  
K. Kefurt ◽  
K. Čapek ◽  
J. Čapková ◽  
Z. Kefurtová ◽  
J. Jarý
Keyword(s):  
Amino Sugars ◽  
Derivatives Of

scholarly journals Amino-sugars enhance recognition and phagocytosis of particles by human neutrophils

Blood ◽  
1983 ◽  
Vol 62 (3) ◽  
pp. 697-701 ◽  
Author(s):  
RL Doolittle ◽  
CH Packman ◽  
MA Lichtman
Keyword(s):  
Human Neutrophils ◽  
Amino Sugars ◽  
Carbohydrate Binding ◽  
Carbohydrate Recognition ◽  
Membrane Structures ◽  
Fluorescent Beads ◽  
Amino Derivatives ◽  
Recognition Systems ◽  
Dose Dependent ◽  
Derivatives Of

Abstract Neutrophils were examined for their ability to recognize and ingest beads coated with amino-derivatives of glucose, mannose, and galactose. Radioactive or fluorescent beads coated with any of the three sugars were ingested to an extent three times that observed with albumin- coated beads. Enhancement of ingestion of sugar-coated beads was much more evident when examined by electron micrographic studies. Inclusion of glucose or mannose in the medium with glucose- or mannose-coated beads caused a dose-dependent reduction of ingestion to control levels, but ingestion of galactose-coated beads was poorly inhibited. Similarly, galactose or fucose (6-deoxy-galactose) markedly inhibited ingestion of galactose-coated beads, but caused only a slight decrease in ingestion of glucose- or mannose-coated beads. Thus, neutrophils possess carbohydrate-binding membrane structures that can mediate recognition and ingestion of sugar-coated beads. Such carbohydrate recognition systems may underlie certain interactions of neutrophils and other surfaces.

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