200941-36-2

Upstream product

• 115792-70-6 1,2,3,4,6‐pentaacetyl L‐mannopyranoside 
• 200941-35-1 phenyl‐2,3,4,6‐tetra‐O‐acetyl‐1‐thio‐α‐L‐mannopyranoside 
• 76-83-5 trityl chloride 
• 200941-62-4 phenyl‐1‐thio‐α‐L‐mannopyranoside 

Downstream Products

• 200941-39-5 Succinic acid mono-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 200941-42-0 Succinic acid (2S,4aS,6R,7S,8R,8aS)-7-benzoyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 200941-45-3 Succinic acid (2S,3R,4S,5R,6R)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 200941-43-1 Succinic acid (2R,3S,4R,5S,6S)-3-benzoyloxy-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 200941-38-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-mannopyranoside 
• 200941-37-3 (2S,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran 

Relevant academic research and scientific papers

Double asymmetric induction during intramolecular glycosylation

N-Iodosuccinimide activation of prearranged glycosides constructed out of phenyl 2,3,4-tri-O-benzyl-1-thio-α-L- and -D-mannopyranosides which are linked by a succinyl spacer via position 6 to position 3 of the benzyl 2-O-benzoyl-6-O-benzyl-α-L- and -D-glucopyranosides (6,3-prearranged L-Man/L-Glc, D-Man/D-Glc, L-Man/D-Glc, and D-Man/L-Glc) affords α/β-mixtures of the corresponding 3,6′-succinyl bridged disaccharides Man-(1→4)-Glc in 70-78% yield. The Diastereoselectivity of the Intramolecular Glycosylation Is Independent of the Topographic Properties of the Prearranged Glycosides (The α-Anomers Predominate for L-Man/L-Glc and D-Man/D-Glc) but Depends on the Geometric Properties (The β-Anomers Predominate for L-Man/D-Glc and D-Man/L-Glc). Thus, a Double Asymmetric Induction Is Operative during Intramolecular Glycosylation of Prearranged Glycosides. Furthermore, the Diastereoselectivity Strongly Depends on the Topological Properties and on the Donor Moiety of the Prearranged Glycosides, since 2,3-prearranged L-Man/D-Glc Affords Solely the Disaccharide α-L-Man-(1→4)-D-Glc whereas the Corresponding L-Rha/D-Glc Was Previously Shown to Give Predominantly the Disaccharide β-L-Rha-(1→4)-D-Glc.