14675-51-5

Upstream product

• 100-02-7 4-nitro-phenol 
• 2873-29-2 D-glucal triacetate 
• 118356-98-2 4,6-di-O-acetyl-3-O-D-glucal 

Downstream Products

• 90114-67-3 (3S)-2t-hydroxymethyl-6c-(4-nitro-phenoxy)-3,6-dihydro-2H-pyran-3r-ol 
• 220758-07-6 4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 220758-16-7 4-nirtophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 273199-63-6 4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 157430-17-6 4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 

Relevant academic research and scientific papers

ZnBr2-catalyzed and microwave-assisted synthesis of 2,3-unsaturated glucosides of hindered phenols and alcohols

GRAPHICAL ABSTRACT Zinc bromide (ZnBr2) under microwave irradiation efficiently catalyzed the Ferrier reaction of hindered phenols and alcohols to afford the corresponding α-2,3-unsaturated glucoside acetates in good yields and with good stereoselectivity. The reaction affords a facile access to new 2,3-dideoxyglucosides of important phenolic and alcoholic constituents of spices.

O- and N-Glycosidation of d-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis

We have disclosed the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity. The reaction would take place via

Scandium triflate catalyzed ferrier rearrangement: An efficient synthesis of 2,3-unsaturated glycopyranosides

Scandium(III) trifluoromethanesulfonate is found to catalyze efficiently the O-glycosidation of 3,4,6-tri-O-acetyl-D-glucal with various alcohols and phenols to afford the corresponding 2,3-unsaturated glycosides in excellent yields with good anomeric selectivity.

An easy and efficient preparation of aryl α-O-Δ2-glycosides

Ferrier reaction between acetylglycals and p-NO2, m-NO2 and p-t-butylphenol after recrystallization gave aryl O-Δ2-glycosides as the pure α anomers. Deacetylation of these compounds and benzylation of the crude diol led to

Reaction of 2,3-unsaturated aryl glycosides with Lewis acids: A convenient entry to C-aryl glycosides

A facile synthesis of 2',3'-unsaturated-C-aryl glycosides by BF3 · Et2O mediated 'O' to 'C' transformation of 2,3-unsaturated aryl glycosides is reported.