117153-58-9

Upstream product

• 67-56-1 methanol 
• 115220-98-9 ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yl)-phosphoramidic acid dimethyl ester 

Downstream Products

• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 10583-67-2 methyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

NOUVELLE VOIE D'ACCES AUX 1,2-trans-2-AMINO-2-DESOXY-GLYCOPYRANOSIDES PAR L'INTERMEDIAIRE DES PHOSPHORAMIDATES DE 1,2-trans-2-DESOXY-2-IODOGLYCOPYRANOSYLES

1,2-trans-2-Deoxy-2-iodoglycopyranosyl phosphoramidates (prepared from the corresponding glycals by addition of iodoazide, followed by Staudinger reaction with a phosphite) led by treatment with an alcohol in the presence of a base to the corresponding 1,2-trans-2-deoxy-2-phosphoramidoglycopyranosides, after inversion of configuration at C-1 and C-2.The reaction proceeded by an aziridine intermediate, which was opened by the alcohol present in the medium.Use of simple alcohols yielded alkyl glycosides having β-D-gluco, β-D-xylo, α-D-manno, and α-D-lyxo configurations, respectively, starting from α-D-manno, α-D-lyxo, β-D-gluco-, and β-D-xylo phosphoramidates, with excellent yields.The same reaction with an alcohol derived from galactopyranose led to the expected disaccharide with a low yield.