857892-43-4

Upstream product

• 3695-77-0 triphenylmethanethiol 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 76-83-5 trityl chloride 
• 57030-42-9 2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 

Downstream Products

• 616238-31-4 triphenylmethyl 1-thio-α-D-mannopyranoside 
• 857892-49-0 2,3,4,6-tetra-O-benzyl-1-doexy-1-thio-α-D-mannopyranose 
• 857892-48-9 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranose 
• 857892-44-5 triphenylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 616238-32-5 (4aR,6R,7S,8R,8aS)-2,2-Dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 616238-33-6 (4aR,6R,7S,8R,8aR)-8-Benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 616238-34-7 Methanesulfonic acid (4aR,6R,7S,8S,8aR)-8-benzyloxy-2,2-dimethyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

A building block approach to the synthesis of a family of S-linked α-1,6-oligomannosides

The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasaccharides. On the other hand, construction from the non-reducing end involved coupling of the above disaccharide thioacetate with an anomeric S-trityl protected 6'-iodo disaccharide. The resulting S-trityl tetrasaccharide was converted to a tetrasaccharide thioacetate, which was coupled with the same anomeric S-trityl protected 6'-iodo disaccharide to afford the hexasaccharide, which was elaborated to the methyl thioglycoside. The developed methodology may prove useful for the construction of other S-linked oligosaccharides.

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.

A general method for the synthesis of sugar 2-C-sulfonic acids by 1 → 2 arylthio group migration in acid-sensitive thioglycosides. Direct transformation of thiotrityl ethers into C-sulfonic acids

(Matrix presented) Fully protected triphenylmethyl 2-O-mesyl-1-thio-β- D-gluco- (14) and -α-D-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 → 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-α-D-manno- (15) and -β-D