222413-89-0

Upstream product

• 93-97-0 benzoic acid anhydride 
• 222413-85-6 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-acetyl-β-D-galactopyranoside 
• 117252-95-6 2-(trimethylsilyl)ethyl β-D-galactopyranoside 
• 222413-76-5 2-(trimethylsilyl)ethyl 6-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 222413-90-3 (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-acetyl-2,4-di-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of ganglioside GM4 analogs as potential immunosuppressive agents 1

An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio β-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonu lopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.