340160-99-8

Basic information

• Product Name: phenyl O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• Synonyms: phenyl O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS NO: 340160-99-8
• Molecular Weight: 790.931
• Mol File: 340160-99-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: phenyl O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside(340160-99-8)
• EPA Substance Registry System: phenyl O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside(340160-99-8)

Safety Data

• Hazardous Substances Data: 340160-99-8(Hazardous Substances Data)

Upstream product

• 516-12-1 N-iodo-succinimide 
• 158716-07-5 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 294643-67-7 ((2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tert-butyl-dimethyl-silane 
• 340160-97-6 ((2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tert-butyl-dimethyl-silane 
• 340160-98-7 [(2R,4aR,6S,7S,8S,8aR)-8-Benzyloxy-6-((2R,4aR,6R,7S,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane 

Downstream Products

• 1144104-37-9 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 340161-01-5 C₉₂H₁₀₀O₂₀SSi 

Relevant articles and documents

Efficient synthesis of α(1,2)-linked oligomannoside derivatives through one-pot glycosylation

An α(1,2)-linked oligomannoside derivative having a free C-2 hydroxyl group and a C-3 pivaloyl group was synthesized from a thiophenyl mannose derivative 1 using a one-pot self-condensation and applying a α-stereoselective procedure. The mannosylation exclusively generated α-mannoside linkages. The observed α-directing effect was rationalized by the remote participation of the pivaloyl group in C-3 position. The polymerization degree was controlled by the promoter amount providing the mannobiose derivative as a major product. Applying this method eliminated many synthetic steps. The α(1,2)-linked oligomannoside derivatives, which are key intermediates for the synthesis of oligomannose type N-glycans for glycoproteins, were easily prepared.

Synthesis of |β-(1→2)-linked oligomannosides

β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of |β-(1→2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β-(1→2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.