13639-55-9

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 75-66-1 2-methylpropan-2-thiol 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 66791-49-9 1-(tert-butylsulfanyl)-2-(trimethylsilyl)ethane 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 94198-62-6 tert-butyl 1-thio-D-glucopyranoside 
• 112288-70-7 (2R,3R,4S,5R)-6,6-Bis-tert-butylsulfanyl-hexane-1,2,3,4,5-pentaol 

Relevant academic research and scientific papers

Silver fluoroborate promoted sulfur alkylation of β-silyl ethyl sulfides. Selective synthesis of β-thioglycosides

Silver (I) activation of α-glucosyl bromide in the presence of 2-trimethylsilylethyl sulfides as sulfur nucleophiles selectively provides β-thioglycosides.

REACTIONS OF D-GLUCOSE, D-XYLOSE, AND D-ERITHROSE WITH 2-METHYL-2-PROPANETHIOL

The reaction of D-glucose and D-xylose with 2-methyl-2-propanethiol in conc. hydrochloric acid yielded tert-butyl 1-thioglycopyranosides (produts of kinetic and thermodynamic control).Di-tert-butyl dithioacetals (12-14) were obtained from the acetylated aldehydo-derivatives of D-glucose, D-xylose, and D-erythrose.On brief treatment with conc. hydrochloric acid, 12 and 13 gave tert-butyl 1-thio-α- and -β-glycopyranosides and 14 gave the corresponding furanosides.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron

A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure β-thioglycosides were obtained in good to high yields with exclusive diastereocontrol.

Involvement of the S-aglycon in the conformational preferences of thioglucosides

The conformational preferences of two series of alkyl β-d-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the nS s(-) σC s(-) O* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds.

Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.

Stereoselective 1,2-CIS-1-thioglycosidation of aldohexoses with tert-butyl mercaptan in 90% trifluoroacetic acid

tert-Butyl 1,2-cis-1-thioglycopyranosides of various aldohexoses (D-glucose, D-galactose, D-mannose, and L-rhamnose), and disaccharides (cellobiose, lactose, and maltose) were preferentially prepared in good yields by reacting the corresponding free sugar