30657-68-2

Upstream product

• 108-93-0 cyclohexanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 108-24-7 acetic anhydride 
• 29781-93-9 cyclohexylglucoside 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 35927-64-1 2-bromoethyl 1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 1037310-48-7 1,4-bis-(1-O-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naphthalene 
• 186135-38-6 (2-hydroxy)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 19879-84-6 tetraacetyl thioglucose 
• 13871-89-1 trimethylsilyl cyclohexyl ether 

Downstream Products

• 6605-39-6 cyclohexyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 5284-99-1 cyclohexyl glucoside 
• 25320-98-3 cyclohexyl glucoside 

Relevant academic research and scientific papers

AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature

Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.

Sulfonated graphene oxide as highly efficient catalyst for glycosylation

Heterogeneous sulfonated graphene oxide for the first time has been used as a green and efficient catalyst for atom-economic glycosylation of unprotected, unactivated glycosyl donors or 2,3,4,6-tetra-O-acetylglycosyltrichloroacetimidate with various accep

Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions

Heterogeneous Bronsted solid acid catalysts have the potential to decrease the environmental impact related to chemical production. Herein, we have synthesized polyvinyl bound trisulfonate ethylamine chloride (PV-THEAC) and polyvinyl bound disulfonate ethylamine (PV-DSEA) as Bronsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions with sugar derivatives. In particular, 0.3 equiv. of the PV-THEAC catalyst was found to be the most efficient and a reusable catalyst for glycosylation reactions. A high density of the trisulfonic group (-OSO3H) contributed to the excellent catalytic activity during glycosylation. Moreover, glycosylation reactions with d-mannose, d-xylose and d-glucose have been studied with alcohol. Remarkable acceleration of the glycosylation reaction using a glycosyltrichloroacetimidate donor was obtained with the selective production of β-glycoside.

Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids

A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr 3 promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

SnCl4- and TiCl4-catalyzed anomerization of acylated O - And S -glycosides: Analysis of factors that lead to higher α: β d reaction rates

The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of α-O- and α-S-glycolipids is discussed. The SnCl4-catalyzed anomerization reactions of β-S- and β-O-glycosides of 18 substrates followed first order equilibrium kinetics and kf + kr values were obtained, where kf is the rate constant for the forward reaction (β → α) and kr is the rate constant for the reverse reaction (α → β). Comparison of the kf + k r values showed that reactions of glucuronic acid or galacturonic acid derivatives were ～10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and α:β ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron releasing generally led to rate enhancements. The anomerization of S-glycosides was consistently faster than that of corresponding O-glycosides. Reactions were generally faster for reactions with TiCl4 than those with SnCl4. Anomeric ratios depended on the Lewis acid, the number equivalents of the Lewis acid, temperature, and substrate. Very high ratios of α-products for both O- and S-glucuronides were observed for reactions promoted by TiCl4; for these substrates TiCl4 was superior to SnCl4. Anomeric ratios from anomerization of S-glucosides were higher with SnCl4 than with TiCl4. The dependence of equilibrium ratio on Lewis acid and the number of equivalents of Lewis acid indicated that the equilibrium ratio is determined by a complex of the saccharide residue bound to the Lewis acid and not the free glycoside. The high α:β ratios observed for anomerization of both O- and S-glycuronic acids can be explained by coordination of the C-1 heteroatom and C-6 carbonyl group of the product to the Lewis acid, which would enhance the anomeric effect by increasing the electron-withdrawing ability of the anomeric substituent and lead to an increase in the proportion of the α-anomer. Such an observation would argue against the existence of a reverse anomeric effect. Support for a chelation-induced endocyclic cleavage mechanism for the anomerization is provided by the trapping of a key intermediate. The data herein will help predict the tendency of β-glycosides to undergo anomerization; this includes cases where 1,2-trans glycosides are initial products of glycosidation reactions catalyzed by TiCl4 or SnCl4.

Highly chemo- and stereoselective glycosidation of permethacrylated O-glycosyl trichloroacetimidate reagents promoted by TMSNTf2

TMSNTf2 has been used efficiently as a promoter in glycosidation reaction involving permethacrylated Schmidt reagents. While TMSNTf2 is known to be a powerful activator for C{double bond, long}O double bonds, we have discovered that this reagent can activate C{double bond, long}N double bond selectively, even in the presence of excess C{double bond, long}O groups of permethacrylated O-glycosyl trichloroacetimidate substrates. Glycosides are synthesized in moderate to reasonable yields with an excellent overall β-stereoselectivity.

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.

Oxidatively induced glycosylation starting from hydroquinone glycosides

As a new class of glycosyl donors, hydroquinone glycosides can be used for glycosylation reactions. Their activation can be performed either electrochemically or under homogeneous chemical conditions. Conventionally, several glucosides were produced with yields greater than 77% using DDQ in CH2Cl2 as oxidizing agent. For electrolyses, glycosides of trimethylhydroquinone are preferably used because their low oxidation potentials allow the utilization of an undivided cell. The synthesis of the glycosyl donors was achieved with high efficiency by direct coupling of the phenols with peracetylated monosaccharides employing boron trifluoride etherate as the catalyst. The oxidation of hydroquinone derivatives can also be applied to the generation of other stabilized cations.

Glycosidation-anomerisation reactions of 6,1-anhydroglucopyranuronic acid and anomerisation of β-D-glucopyranosiduronic acids promoted by SnCl 4

The reaction of silylated nucleophiles with 6,1-anhydroglucopyranuronic acid (glucuronic acid 6,1-lactones) catalysed by tin(IV) chloride provides 1,2-trans or 1,2-cis (deoxy)glycosides in a manner dependent on the donor structure. The α-glycoside was obt