59263-36-4

Upstream product

• 126660-01-3 (3aR,5R,6S,7S,7aR)-2-Benzyloxy-6-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-hydroxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-ol 
• 123170-24-1 O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 
• 123170-25-2 Acetic acid (2S,3R,4S,5R,6R)-2,4-bis-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 126660-00-2 O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 
• 103136-46-5 Allyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 126659-99-2 O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl bromide 
• 130564-24-8 Acetic acid (3aS,4R,6S,7R,7aS)-4-acetoxymethyl-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 100-39-0 benzyl bromide 
• 197235-72-6 (3R,4R,5S,6R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 75795-58-3 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose 
• 197235-74-8 [(2R,3R,4S,5R,6R)-2,4-Bis-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy]-dimethyl-(1,1,2-trimethyl-propyl)-silane 
• 123170-25-2 Benzyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-O-acetyl-3,6-di-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 123170-26-3 Benzyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-O-pivaloyl-3,6-di-O-benzyl-β-D-glucopyranoside 
• 123170-18-3 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2,4-bis-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 123170-26-3 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2,4-bis-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 123170-18-3 benzyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Efficient synthesis of ganglioside GM2 for use in cancer vaccines

A target antigen for cancer immunotherapy, ganglioside GM2, is expressed on the cell surface of several human cancer types. An efficient chemical synthesis can now make available ample amounts of a structurally well-defined synthetic GM2, free of biological contaminants. This greatly facilitates the systematic construction of safe and efficient GM2 cancer vaccines.

An efficient synthesis of ganglioside GM3: highly stereocontrolled glycosylation by use of auxiliaries

An efficiently stereocontrolled total synthesis of GM3 α-D-Neup5Ac-(2->3)-β-D-Galp-(1->4)-β-D-Glcp-(1->1)-Cer as achieved by employing both methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-bromo-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate for the key sialylation step, and O--(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate and fluoride for the key coupling step with a ceramide derivative.These two steps were significantly altered and improved in comparison with our previous synthesis that had been executed without use of stereocontrolling auxiliaries.GM3 was obtained in 4.5percent overall yield in 19 steps starting from allyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside.