64495-83-6

Basic information

• Product Name: cyclohexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• CAS NO: 64495-83-6
• Molecular Weight: 446.519
• Mol File: 64495-83-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: cyclohexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside(64495-83-6)
• EPA Substance Registry System: cyclohexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside(64495-83-6)

Safety Data

• Hazardous Substances Data: 64495-83-6(Hazardous Substances Data)

Upstream product

• 1569-69-3 Cyclohexanethiol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 66108-02-9 1-Cyclohexylthio-β-D-glucose 

Relevant articles and documents

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.

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Facile preparation of α-glycosyl iodides by in situ generated aluminum iodide: Straightforward synthesis of thio-, seleno-, and o-glycosides from unprotected reducing sugars

A facile and practical protocol was developed for the synthesis of glycosyl iodides using AlI3 generated in situ from cheap aluminum metal and molecular iodine. Furthermore, in combination with iodine-catalyzed per-O-acetylation, sequential synthesis of per-acetylated glycosyl iodides, per-acetylated thioglycosides, selenoglycoside, and O-glycosides from unprotected reducing sugars was also achieved with complete diastereocontrol in a one-pot version. Supplemental material is available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. Copyright Taylor & Francis Group, LLC.