213998-08-4

Basic information

• Product Name: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• Synonyms: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS NO: 213998-08-4
• Molecular Weight: 536.646
• Mol File: 213998-08-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside(213998-08-4)
• EPA Substance Registry System: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside(213998-08-4)

Safety Data

• Hazardous Substances Data: 213998-08-4(Hazardous Substances Data)

Upstream product

• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 108-98-5 thiophenol 
• 108-24-7 acetic anhydride 
• 210295-06-0 phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 86651-41-4 methyl 3,6-di-O-pivaloyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 158716-08-6 phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 

Downstream Products

• 635316-98-2 (2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-fluoro-6-hydroxymethyl-tetrahydro-pyran-4-ol 
• 80738-57-4 methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 1096119-89-9 6'-azidohexyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside 

Relevant articles and documents

Stereoselective β-Mannosylation by Neighboring-Group Participation

The stereoselective synthesis of glycosidic bonds is the main challenge of oligosaccharide synthesis. Neighboring-group participation (NGP) of C2 acyl substituents can be used to provide 1,2-trans-glycosides. Recently, the application of NGP has been extended to the preparation of 1,2-cis-glycosides with the advent of C2 chiral auxiliaries. However, this methodology has been strictly limited to the synthesis of 1,2-cis-gluco-type sugars. Reported herein is the design and synthesis of novel mannosyl donors which provide 1,2-cis-mannosides by NGP of thioether auxiliaries. A key element in the design is the use of1C4locked mannuronic acid lactones to enable NGP of the C2 auxiliary. In addition to C2 participation a new mode of remote participation of the C4 benzyl group was identified and provides 1,2-cis-mannosides.

Synthesis of an octamannosyled glycan chain, the key oligosaccharide structure in ER-associated degradation

The high-mannose type decasaccharide (Man8GlcNAc2), the proposed ligand of ER residing mannosidase-like proteins (MLP), and its monoglycosylated homologue (α-Glc1Man8GlcNAc 2) were synthesized. The oligosaccharide assembly was performed in a convergent and stereoselective manner, using three oligosaccharide components, a core trisaccharide having a β-mannoside bond, a liner mannotriose, and a branched mannotetraose.