1072440-22-2

Upstream product

• 67-56-1 methanol 
• 1072440-17-5 tert-butyl (3S,7S,Z)-2-oxo-7-((1R,2R,3R)-1,2,4-tris(benzyloxy)-3-hydroxybutyl)-2,3,4,7-tetrahydrooxepin-3-ylcarbamate 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 93125-77-0 (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol 

Downstream Products

• 1072440-16-4 (2R)-methyl 4-((3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2-yl)-2-(tert-butoxycarbonylamino)butanoate 
• 1442044-34-9 C₃₇H₄₅NO₉ 
• 1442044-21-4 (S)-methyl 4-((2S,3S,4R,5R,6R)-4,5-di(benzyloxy)-6-((benzyloxy)-methyl)-3-hydroxytetrahydro-2H-pyran-2yl)-2-((tert-butoxycarbonyl)amino)butanoate 
• 1442044-28-1 (S)-methyl 4-((2S,3S,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2yl)-2-((tert-butoxycarbonyl)amino)butanoate 

Relevant academic research and scientific papers

Synthesis of β-C-GlcNAc ser from β-C-Glc ser

The glycosylation of proteins, specifically installation of O-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.

Syntheses of α- and β-C-glucopyranosyl serines from a common intermediate

(Chemical Equation Presented) A versatile synthesis leading to either C-linked α- or β-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the α-linkage. A transposition of these last steps leads to the α-linked isomer selectively.