88713-65-9

Upstream product

• 72471-11-5 methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 501-53-1 benzyl chloroformate 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 

Relevant academic research and scientific papers

Intramolecular Metal-Free C(sp3)-H Activation Enables a Selective MonoO-Debenzylation of Fully Protected Aminosugars

Carbamate-bearing benzylated aminosugars undergo an I2/I(III)-promoted intramolecular hydrogen atom transfer (IHAT) followed by a nucleophilic attack to provide polycyclic structures. Thus, suitably positioned benzyl ethers are surgically oxidized into the corresponding mixedN/O-benzylidene acetals, which can be conveniently deprotected under mild acidic conditions to grant access to selectivelyO-deprotected aminosugars amenable for further derivatization. The scope of this strategy has been proven with a series of furanosic and pyranosic scaffolds. Preliminary mechanistic studies, including Hammett LFER and KIE analyses, support a reaction pathway with nucleophilic cyclization as the rate-determining step.

SYNTHESIS OF METHYL 2,3-O-D-GLYCOPYRANOSYLIDENE α-D-MANNOPYRANOSIDES HAVING VARIOUS SUBSTITUENTS

The title compounds were obtained by condensation of D-glucono-, D-galactono-, or L-glycero-D-gluco-heptono-1,5-lactones with methyl 2,3-di-O-(trimethylsilyl)-α-D-mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsil