182118-72-5

Upstream product

• 100-51-6 benzyl alcohol 
• 182118-63-4 allyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 119237-96-6 allyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 155835-93-1 allyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 182265-63-0 allyl 2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 

Downstream Products

• 182118-81-6 2,2,2-Trichloro-acetimidic acid (2S,4aR,6R,7R,8S,8aS)-8-[(2S,4aR,6S,7R,8R,8aR)-7-azido-2-phenyl-8-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 

Relevant academic research and scientific papers

Total synthesis of sialylgalactosylgloboside: Stage-specific embryonic antigen 4

A versatile total synthesis of sialylgalactosylgloboside (SGG, 1), carrying the stage-specific embryonic antigen 4 (SSEA-4) is reported, illustrating a more general strategy for the synthesis of complex globo-series glycosphingolipids. Starting from readily available building blocks 7, 8, and 10, two different approaches to the synthesis of the key tetrasaccharide 6 have been developed in a highly convergent manner. Further glycosylations with galactosyl trichloroacetimidate (5) and sialyl phosphite (2) donors successively afforded the penta- and hexasaccharides 3 and 11. The latter was finally converted into the target molecule (SGG, 1) with the help of a azidosphingosine glycosylation procedure, favored in this case by the stereocontrolling properties of the 2a-O-pivaloyl protecting group. Valuable intermediates 6 and 3, having the oligosaccharidic skeletons of Gb4 and Gb5 (SSEA-3), respectively, were obtained in the course of the synthesis.