351209-68-2

Upstream product

• 65207-55-8 D-lactal 
• 100-39-0 benzyl bromide 
• 351209-67-1 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide 
• 51450-24-9 hexa-O-acetyl-D-lactal 
• 895140-70-2 (2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-ylamine 
• 85-44-9 phthalic anhydride 
• 132911-87-6 4-=-(3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-D-arabino-hex-1-enitol 
• 132911-84-3 4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol 

Downstream Products

• 895140-71-3 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 

Relevant academic research and scientific papers

A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15→18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34→36). Another key strategic element involved the epimerization of an interior core glucoside to reach the β-mannoside (see 37→38) required in the ring C sugar of the high mannose core.