64495-84-7

Basic information

• Product Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-cyclohexylsulfanyl-tetrahydro-pyran-3-yl ester
• Synonyms: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-cyclohexylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS NO: 64495-84-7
• Molecular Weight: 446.519
• Mol File: 64495-84-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-cyclohexylsulfanyl-tetrahydro-pyran-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-cyclohexylsulfanyl-tetrahydro-pyran-3-yl ester(64495-84-7)
• EPA Substance Registry System: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-cyclohexylsulfanyl-tetrahydro-pyran-3-yl ester(64495-84-7)

Safety Data

• Hazardous Substances Data: 64495-84-7(Hazardous Substances Data)

Upstream product

• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 1569-69-3 Cyclohexanethiol 
• 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 
• 37556-51-7 S-cyclohexyl 4-methylbenzenesulfonothioate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Downstream Products

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

Relevant articles and documents

Anodic Reactivity of Alkyl S-Glucosides

A voltammetric study of a series of alkyl and aryl S-glucosides unveiled the reactivity patterns of alkyl S-glucosides toward anodic oxidation and found noteworthy differences with the trends followed by aryl derivatives. The oxidation potential of alkyl S-glucosides, estimated herein from square-wave voltammetry peak potentials (Ep), depends on the steric properties of the aglycone. Glucosides substituted with bulky groups exhibit Ep values at voltages more positive than the values of those carrying small aglycones. This relationship, observed in all analyzed alkyl series, is evidenced by good linear correlations between Ep and Taft's steric parameters (ES) of the respective alkyl substituents. Moreover, the role of the aglycone's steric properties as a primary reactivity modulator is backed by poor correlations between Ep and the radical stabilization energies (RSEs) of the aglycone-derived thiyl radicals (RS?). In contrast, aryl glucosides' Ep values exhibit excellent correlations with the aryl substituents' Hammett parameters (σ+) and the ArS?RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside's electrochemical reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective group's effect on Ep. Alkyl S-glucosides' reactivity proved to be more sensitive to protective group exchange.

Synthesis of glycosyl sulfoximines by a highly chemo- And stereoselective NH- And O-transfer to thioglycosides

A synthesis of unprecedented and stable glycosyl sulfoximines is reported. The developed strategies represent the first example of highly stereoselective sulfoximine formation directly from thioglycosides. This synthetic protocol has been tested on severa

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.