260779-95-1

Upstream product

• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 98-88-4 benzoyl chloride 
• 1352561-95-5 phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside 

Downstream Products

• 260779-99-5 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-6-O-benzyl-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 260780-00-5 phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate 
• 260779-98-4 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-4,6-O-benzylidene-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Prearranged glycosides, 9. - Chemical synthesis of a tetrasaccharide fragment related to the exopolysaccharide of Arthrobacter sp. CE-17

The tetrasaccharide 5-aminopentyl glycoside β-D-Manp-(1→4)-β-D-Glcp- (1→4)-α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NH2(22) related to the exopolysaccharide of Arthrobacter sp. CE-17 was synthesized by coupling of the properly protected disaccharide blocks β-D-Manp-(1→4)-β-D-Glcp-1-S-Ph (11) and α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NHZ (20). Building block 11 was obtained by intramolecular β-mannosylation of a malonyl-tethered disaccharide glycoside which was prepared from phenyl 4,6-O-benzylidene-1- thio-β-D-glucopyranoside (1) and ethyl 2,3,4-tri-O-benzyl-1-thio-α-D- mannopyranoside (5) in 5 steps. Building block 20 was obtained by coupling N- Z-protected 5-aminopentyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (14) obtained from the non-benzylated counterpart 12 with ethyl 2,3-di-O- benzoyl-4-O-chloroacetyl-1-thio-α-L-rhamnopyrano- side (18) obtained in 3 steps from ethyl 2,3-O-isopropylidene- 1-thio-α-L-rhamnopyranoside (15).