4291-68-3

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 81336-89-2 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triol 
• 53081-30-4 tetra-O-benzyl-α-D-galactosyl bromide 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 97205-08-8 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 108-98-5 thiophenol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 785806-29-3 thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 122204-35-7 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-galactopyranoside 
• 122204-36-8 methyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 93414-71-2 2'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)furan 
• 93414-72-3 (1R)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-C-(2-thienyl)-D-glucitol 
• 82300-67-2 1-deoxy-1-(C-2',4',6'-trimethoxyphenyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 115969-49-8 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 117253-13-1 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 82805-17-2 methyl hepta-O-benzyl-β-cellobioside 
• 82805-15-0 C₆₂H₆₆O₁₁ 
• 135080-50-1 (1α,4aβ,8α,8aα)-Decahydro-8-hydroxy-1-naphthyl 2,3,4,6-Tetra-O-benzyl-α-D-Glucopyranoside 
• 135080-50-1 (1R,4aR,8S,8aR)-8-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ol 
• 135080-50-1 (1S,4aS,8R,8aS)-8-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ol 
• 135080-50-1 (1R,4aR,8S,8aR)-8-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ol 
• 174402-48-3 12,13-dihydro-2,10-dibenzyloxy-13-(β-D-2,3,4,6-tetra-O-benzylglucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-methyl-5,7(6H)-dione 

Relevant academic research and scientific papers

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy

Method for preparing halogenated sugar under mild conditions

The invention discloses a method for preparing halogenated sugar under mild conditions. The method comprises the following steps that an easily-prepared thioglycoside donor and a halogen simple substance or halogen intercompound undergo a reaction at room temperature to obtain the halogenated sugar (chlorine, bromine and iodine). The halogen simple substance or the halogen intercompound is commercial easily available iodine elementary substance, iodine bromide and iodine chloride. The method is suitable for various pyranoses and furanoses. The method has no limitation on a protecting group ofthe thioglycoside donor, and the protecting group can be an electron withdrawing group such as acetyl, benzoyl and the like, and can also be an electron donating group such as benzyl, silicon base andthe like. Meanwhile, the reaction can occur in various organic solvents such as dichloromethane, acetonitrile and methylbenzene. The preparation method of the halogenated sugar is simple, reaction conditions are mild, raw materials are easy to obtain, the application range is wide, the halogenated sugar is compatible with acid-labile groups such as isopropylidene ketal and silicon groups, and a pure product can be obtained by removing a solvent from the halogenated sugar which is not stable in the separation process.

Solvent-free, under air selective synthesis of α-glycosides adopting glycosyl chlorides as donors

α-Glycosides are highly relevant synthetic targets due to their abundance in natural oligosaccharides involved in many biological processes. Nevertheless their preparation is hampered by several issues, due to both the strictly anhydrous conditions typically required in glycosylation procedures and the non-trivial achievement of high α-stereoselectivity, one of the major challenges in oligosaccharide synthesis. In this paper we report a novel and efficient approach for the highly stereoselective synthesis of α-glycosides. This is based on the unprecedented solvent-free combination of triethylphosphite, tetrabutylammonium bromide and N,N-diisopropylethylamine for the activation of glycosyl chlorides under air. Despite the relative stability of glycosyl chlorides with respect to more reactive halide donors, the solvent-free procedure allowed a wide set of α-glycosides, including biorelevant fragments, to be obtained in much shorter times compared with similar glycosylation approaches in solution. The presented method features a wide target scope and functional group compatibility, also serving with partially disarmed substrates, and it does not require a high stoichiometric excess of reagents nor the preparation of expensive precursors. The solvent-free glycosylation can be even directly performed from 1-hydroxy sugars without purification of the in situ generated chloride, providing an especially useful opportunity in the case of highly reactive and labile glycosyl donors. This journal is

Synthesis of glycosyl chlorides using catalytic Appel conditions

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, thos

Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system

Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone

Acceptor-influenced and donor-tuned base-promoted glycosylation

Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.