Synthesis of bis-(methyl 3,4,6-tri-O-acetyl-D-glucopyranosid-2-yl)-oxamides.
The synthesis of a new bis-(D-glucopyranosid-2-yl)oxamides via the key intermediate, N-acetyl N-(methyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranosid-2-yl) oxamic acid chloride (2alpha) is described. Treatment of compound 2alpha with methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranoside afforded N-(methyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranosid-2-yl)-N'-(methyl 3,4,6-tri-O-acetyl-beta-D-glucopyranosid-2-yl)-oxamide. Reaction of 2alpha with 1,2-diaminoethane afforded 1,2-bis-[N,N'-(methyl 3',4',6'-tri-O-acetyl-alpha-D-glucopyranosid-2'-yl)]ethyloxamide as a main product, while 2-N-[N'-(methyl 3',4',6'-tri-O-acetyl-alpha-D-glucopyranosid-2'-yl)oxamide]-ethyl acetamide was formed as a side product. Reaction of 2alpha with 1,3-diamino-2-hydroxypropane gave only 1,3-bis-N,N-[N'-(methyl 3',4',6'-tri-O-acetyl-2'-deoxy-alpha-D-glucopyranosid-2'-yl)-oxamido]-2-propanol.
Temeriusz
Andrzej
A
Department of Chemistry, Warsaw University, Warszawa 02093, Pasteura 1, Poland. atemer@chem.uw.edu.pl
Rowińska
Magdalena
M
Piekarska-Bartoszewicz
Bogusława
B
D002240:Carbohydrate Sequence; D005960:Glucosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C504017:1,2-bis(N,N'-(methyl 3',4',6'-tri-O-acetylglucopyranosid-2'-yl))ethyloxamide; D005960:Glucosides; C504016:N-(methyl 3,4,6-tri-O-acetylglucopyranosid-2-yl)-N'-(methyl 3,4,6-tri-O-acetylglucopyranosid-2-yl)-oxamide; C504015:N-acetyl N-(methyl 3,4,6-tri-O-acetylglucopyranosid-2-yl) oxamic acid chloride; D010072:Oxamic Acid