163955-47-3

Upstream product

• 187139-92-0 octyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 111-88-6 Octanethiol 

Downstream Products

• 187140-05-2 octyl (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-1-thio-α-D-mannopyranoside 
• 187140-02-9 octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-1-thio-α-D-mannopyranoside 
• 187139-98-6 octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-thio-α-D-mannopyransoside 

Relevant academic research and scientific papers

Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-D-glycopyranosides

This paper describes the synthesis, purification, and liquid- crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2. The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S(A) phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety.

Synthesis of alkyl and cycloalkyl α-D-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay

The synthesis of a series of alkyl (having from C6 to C20 aglycones), cyclohexyl, and cyclohexylalkyl α-Dmannopyranosides, 6-deoxygenated analogs, thioglycosides, and sulfones derived thereof, is reported. Here, under the in vitro assay conditions used, n

Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure α-D-Manp-(1→2)-α-D-Manp-(1→6)-α-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D -mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic α-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MITat 1.4, MITat 1.2, and MITat 1.5, respectively.