Methyl 2-benzamido-2-deoxy

M. W. Homer, L. Hough, and A. C. Richardson, Selective benzoylation of methyl 2-benzamido-2-deoxy-a-D-glucopyranoside A convenient preparation of derivatives of 2-amino-2-deoxy-D-galactose, /. Chem. Soc., Sect. C (1970) 1336-1340. 

Gigg and Warren cyclized the methyl 2-benzamido-2-deoxy-5,6-0-isopropylidene-4-0-methylsulfonyl-)8-D-glucopyranoside 135 to the furo-[3,4-d]oxazin-6-yl acyclo C-nucleoside 142 by treatment with sodium meth-oxide in methanol [65JCS1351, 65TL1303 66JCS(C)1872] (Scheme 43). 

R. Khan and L. Hough, Nucleophilic replacement reactions of sulfonates. Part VII. Selective tosylation of methyl 2-benzamido-2-deoxy-a-D-gIucopyranoside and a synthesis of methyl... 

Mesyl Methyl 2-benzamido-2-deoxy-3-0-mesyl-[Pg.726]

Trimesyl Methyl 2-benzamido-2-deoxy-3,4,6-tri-O-mesyl-a-D-glucopyranoside... 

Methyl 2-benzamido-2-deoxy-4,6-di- 0 -tosyl-a-D-glucopyranoside, M-154 Methyl 2-benzamido-2-deoxyglucopyranoside, M-154 Methyl 3-benzamido-3-deoxy-a-D-mannopyranoside, A-313 Methyl 2-benzamido-2-deoxy-3-0-mesyl-a-D-glucopyranoside, M-154 Methyl 2-benzamido-2-deoxy-3-0-methyl-p-D-glucopyranoside, M-154 Methyl 2-benzamido-2-deoxy-3,4,6-tri-O -mesyl-a-D-glucopyranoside, M-154 Methyl 2-benzamido-2-deoxy-3,4,6-tri-0-methyl-a-D-glucopyranoside, M-154... 

Interestingly, methyl 2-deoxy-2-(p-nitrobenzamido)- and -(p-amino-benzamido)-o -D-galactopyranoside were the most potent inhibitors tested.199 These data suggest that, on the protein, there may be a region that can interact specifically with an aromatic moiety at C-2 of 2-amino-2-deoxy-D-galactose. Table XII presents some representative, inhibition data. 

The conversion of 3-amino-3-deoxy sugars into pyrrolidines requires the presence of a leaving group, such as a p-tolylsulfonyloxy group on C-6 this is exemplified by the conversion of 3-azido-3-deoxy-l,2-0-isopropylidene-6-0-p-tolylsulfonyl-a-D-glucofuranose (44) and methyl 3-azido-2-benzamido-2,3-dideoxy-6-0-p-tolylsulfo-nyl-j8-D-glucopyranoside (46) into the respective pyrrolidines, 45 and 47, by reduction of the azido group, followed by cyclization.37... 

In addition to the cyclization of 2-acylamido groups with C-l, the 2-acylamido group can form an oxazoline with C-3. The 2-methyl-oxazolines, which are readily hydrolyzed, have not been isolated, but their probable presence is indicated by the inversion observed.144 For a 2-benzamido group adjacent to a suitable leaving-group on C-3, the oxazolines formed are quite stable and can be isolated. The reaction has been conducted on pyranoside derivatives, 37,173-175 such as methyl 2-benzamido-4,6-0-benzylidene-2-deoxy-3-0-(methylsul-fonyl)-jQ-D-glucopyranoside (137) to give 138, furanoside deriva-... 

Baker and Buss425 used the Pfitzner-Moffatt procedure (phosphoric acid-A /V -dicyclohexylcarbodiimide dimethyl sulfoxide) for the preparation of methyl 3-benzamido-4,6-0-benzylidene-3-deoxy-Q -D-uraZ) o-hexopyranosid-2-ulose and methyl 2-benzamido-4,6-(3-benzylidene-2-deoxy-a-i>n/ >o-hexo-pyranosid-3-ulose in yields of 90%. 

A number of epimino sugars have been prepared by the action of lithium aluminum hydride in tetrahydrofuran on vicinal benzamido sulfonates oriented in the trans relationship. Treated in this way, methyl 3 - benzamido -4,6-0 -benzylidene - 3 - deoxy -2-0- (methylsul-fonyl)-a -D-altropyranoside afforded - methyl 4,6-O-benzylidene-... 

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