474427-03-7

Upstream product

• 82970-25-0 2,3,4-tri-O-acetyl-β-D-glucopyranurono-6,1-lactone 
• 108-95-2 phenol 
• 1529-17-5 phenyltrimethylsilyl ether 
• 62133-77-1 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 
• 474426-72-7 acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride 

Downstream Products

• 110537-90-1 1-O-phenyl-Δ⁴-α-D-glucopyranuronic acid 

Relevant academic research and scientific papers

Glycosidation-anomerisation reactions of 6,1-anhydroglucopyranuronic acid and anomerisation of β-D-glucopyranosiduronic acids promoted by SnCl 4

The reaction of silylated nucleophiles with 6,1-anhydroglucopyranuronic acid (glucuronic acid 6,1-lactones) catalysed by tin(IV) chloride provides 1,2-trans or 1,2-cis (deoxy)glycosides in a manner dependent on the donor structure. The α-glycoside was obt

Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

(graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.