857892-49-0

Upstream product

• 857892-43-4 triphenylmethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 616238-31-4 triphenylmethyl 1-thio-α-D-mannopyranoside 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 857892-45-6 triphenylmethyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 

Downstream Products

• 935666-38-9 chloromethyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 1052273-95-6 C₄₀H₄₀O₆S₂ 
• 149561-02-4 2,3,4,6-tetra-O-benzyl-1-thio-D-mannono-1,5-O-lactone 
• 1433190-41-0 C₃₇H₄₂O₆S 
• 1433190-77-2 C₃₈H₄₄O₆S₂ 
• 97321-70-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-manno-hept-1-enitol 
• 935666-45-8 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl chloromethyl sulfone 

Relevant academic research and scientific papers

Synthesis of Mannosidase-Stable Man3and Man4Glycans Containing S-linked Manα1→2Man Termini

Oligomannose glycans are of interest as HIV vaccine components, but they are subject to mannosidase degradation in vivo. Herein, we report the synthesis of oligosaccharides containing a thio linkage at the nonreducing end. A thio-linked dimannose donor participates in highly stereoselective glycosylations to afford trimannose and tetramannose fragments. Saturation transfer difference nuclear magnetic resonance (STD NMR) studies show that these glycans are recognized by HIV antibody 2G12, and we confirm that the reducing terminal S-linkage confers complete stability against x. manihotis mannosidase.

Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions

Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlle

Synthesis of glycosylthiols and reactivity studies

The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-α-d- glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the α-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.

2-Haloethyl 1-thioglycosides as new tools in glycoside syntheses. Part 1: Preparation, characteristics, general reactions

2-Haloethyl 1-thioglycosides are excellent leaving groups when the 2-haloethyl function is activated with silver salts or Lewis acids. These thioglycosides can be synthesized on the original Cerny route or for better compatibility with the needs of a more complex glycoside synthesis, in stepwise procedures via 2-(2-tetrahydropyran-2-yloxy)ethyl glycosides or trityl 1-thioglycosides. The initial step in glycosidation reaction presumably proceeds via a thiiranium ion, which is responsible for their increased reactivity compared with normal thioethers as leaving groups in glycoside syntheses. Basic features of this new system with respect to reactivity and selectivity in disaccharide syntheses are described.