200941-35-1

Upstream product

• 115792-70-6 1,2,3,4,6‐pentaacetyl L‐mannopyranoside 
• 108-98-5 thiophenol 
• 153830-26-3 1,2,3,4,6‐Pentaacetyl α/β‐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 
• 200941-37-3 (2S,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran 
• 200941-36-2 phenyl 6-O-trityl-1-thio-α-L-mannopyranoside 
• 200941-38-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-mannopyranoside 
• 264128-16-7 Octadecyl-carbamic acid (2S,3S,4R,5R,6S)-2-(acetylamino-methyl)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-pyran-3-yl ester 
• 264128-12-3 Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 264128-10-1 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,4aS,6S,7R,8R,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 264128-15-6 N-{(2S,3S,4R,5R,6S)-4,5-Bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl}-acetamide 
• 264128-13-4 1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Azidomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione 
• 264128-14-5 1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione 
• 264128-11-2 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Syntheses of L‐rhamnose‐linked amino glycerolipids and their cytotoxic activities against human cancer cells

A major impediment to successful cancer treatment is the inability of clinically available drugs to kill drug‐resistant cancer cells. We recently identified metabolically stable L‐glucosaminebased glycosylated antitumor ether lipids (GAELs) that were cytotoxic to chemotherapy‐resistant cancer cells. In the absence of commercially available L‐glucosamine, many steps were needed to synthesize the compound and the overall yield was poor. To overcome this limitation, a facile synthetic procedure using commercially available L‐sugars including L‐rhamnose and L‐glucose were developed and the L‐GAELs tested for anticancer activity. The most potent analog synthesized, 3‐amino‐1‐O‐hexadecyloxy‐2R‐(O–α‐L‐rhamnopyranosyl)‐sn‐ glycerol 3, demonstrated a potent antitumor effect against human cancer cell lines derived from breast, prostate, and pancreas. The activity observed was superior to that observed with clinical anticancer agents including cisplatin and chlorambucil. Moreover, like other GAELs, 3 induced cell death by a non‐membranolytic caspase‐independent pathway.

Novel carbohydrate scaffolds. Assembly of a uridine-mannose scaffold based on tunicamycin

A disaccharide scaffold based on tunicamycin was synthesized from D- uridine and L-mannose. The key step in disaccharide assembly was a β- mannosylation performed using Crich's modification of the sulfoxide glycosylation method. The scaffold described contains two orthogonal derivatization sites and will be used in the search for novel biologically active compounds. (C) 2000 Elsevier Science Ltd.

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.