Brief introduction of (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

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Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In homogeneous catalysis, catalysts are in the same phase as the reactants.74808-09-6, C36H36Cl3NO6. A document type is Article, introducing its new discovery., Reference of 74808-09-6

The development and mechanistic investigation of a highly stereoselective methodology for preparing alpha-linked-urea neo-glycoconjugates and pseudo-oligosaccharides is described. This two-step procedure begins with the selective nickel-catalyzed conversion of glycosyl trichloroacetimidates to the corresponding alpha-trichloroacetamides. The alpha-selective nature of the conversion is controlled with a cationic nickel(II) catalyst, [Ni(dppe)(OTf)2] (dppe=1,2-bis(diphenylphosphino)ethane, OTf=triflate). Mechanistic studies have identified the coordination of the nickel catalyst with the equatorial C2-ether functionality of the alpha-glycosyl trichloroacetimidate to be paramount for achieving an alpha-stereoselective transformation. A cross-over experiment has indicated that the reaction does not proceed in an exclusively intramolecular fashion. The second step in this sequence is the direct conversion of alpha-glycosyl trichloroacetamide products into the corresponding alpha-urea glycosides by reacting them with a wide variety of amine nucleophiles in presence of cesium carbonate. Only alpha-urea-product formation is observed, as the reaction proceeds with complete retention of stereochemical integrity at the anomeric C-N bond.

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Tetrahydropyran – Wikipedia,
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O – Trichloroacetimidates can be prepared, under mild conditions in high yield and high purity, by reacting the substrate with trichloroacetonitrile in dichloromethane and 50% aqueous potassium hydroxide mixture containing a catalytic amount of tetra-n-butylammonium hydrogen sulfate.

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Tetrahydropyran – Wikipedia,
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The transformation of simple hydrocarbons into more complex and valuable products has revolutionised modern synthetic chemistry. This type of reactivity has quickly become one of the cornerstones of modern catalysis . 74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate, molecular formula is C36H36Cl3NO6. In a Article,once mentioned of 74808-09-6, Electric Literature of 74808-09-6

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described. The conditions are practical and do not require the use of molecular sieves with products being isolated in good to high yields.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

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Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature. We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.

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Tetrahydropyran – Wikipedia,
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A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the alpha-amino acid side chain at the anomeric carbon of sugars. This new functionalized silyl enol ether was prepared in multigram scale and high enantiomeric purity starting from methyl N-Boc-L-threoninate (six steps, 49% yield). This reagent was employed in two synthetic approaches to C-glycosyl amino acids. In one approach, the BF3 · Et2O-promoted coupling with tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate afforded the alpha-linked C-glycoside as main product (30% isolated yield), which upon treatment with tert-butyllithium was converted into the beta-linked isomer. Deoxygenation of these compounds by the Barton- McCombie method and unmasking of the glycyl moiety from the oxazolidine ring by oxidative cleavage with the Jones reagent gave the C-glycosyl serine isosteres alpha- and beta-Gal-CH2-Ser. In a similar way were prepared alpha- and beta- Glc-CH2-Ser starting from tetra-O-benzyl-D-glucopyranosyl trichloroacetimidate. In a second approach, the same oxazolidine silyl enol ether was condensed with formyl tetra-O-benzyl-beta-D-C-galactopyranoside in the presence of BF3 · Et2O to give the beta-linked C-glycoside in 78% yield without any anomerization. The deoxygenation of this product and the cleavage of the oxazolidine ring as described above afforded the glycosyl asparagine isostere beta-Gal-(CH2)2-Asn. The same reaction sequence was applied to convert formyl tetra. O-benzyl-beta-D-C-glucopyranoside and mannopyranoside into the C-glycosyl amino acids beta-Glc(CH2)2-Asn and beta-Man-(CH2)2-Asn, respectively.

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Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations.74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate, molecular formula is C36H36Cl3NO6. In a Article,once mentioned of 74808-09-6, Synthetic Route of 74808-09-6

The development of a new glycosylation method for efficient stereoselective synthesis of beta-gluco- and galactosides from their corresponding armed trichloroacetimidate donors mediated by 10 mole% of FeCl3 has been focused. FeCl3 has also been applied to a number of glucose, galactose, mannose and rhamnose based trichloroacetimidate donors with various protecting groups incorporated at the C-2-position to prepare a variety of disaccharides and trisaccharides with excellent 1,2-trans selectivity. FeCl3 can also modulate the 1,2-trans selectivity of the reaction of 2-O-alkylated gluco- and galacto-pyranosyl trichloroacetimidates with phenolic compounds leading to the generation of the corresponding beta-O-aryl glycosides in excellent yield and selectivity. Apart from these the present methodology has been successfully utilized for double glycosylation and orthogonal glycosylation reactions along with its application in one-pot three component orthogonal glycosylation reactions for synthesis of a trisaccharide.

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Having gained chemical understanding at molecular level, chemistry graduates may choose to apply this knowledge in almost unlimited ways, as it can be used to analyze all matter and therefore our entire environment. Like 74808-09-6, Name is (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate. In a document type is Article, introducing its new discovery. COA of Formula: C36H36Cl3NO6

Different from most carbonates the allyloxy carbonyl protecting group can be cleaved under neutral conditions using metal catalysis. However, most of the catalysts employed to date are based upon precious metals. Herein we present two protocols for the mild Fe-catalyzed liberation of alcohols from allylcarbonates that are characterized by broad functional group tolerance and exclusive chemoselectivity.

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1,2-Dimethoxyethane (DME) is shown to be a suitable co-solvent for sensibly improving the alpha-selectivity of glycosidations performed with trihaloacetimidate donors. This solvent works equally well by using either moisture stable Yb(OTf)3 or standard TMSOTf as the promoters.

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Properties and Exciting Facts About (2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

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Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization.The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.

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The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present invention relates to novel glycoconjugated compounds comprising oligosaccharides or polysaccharides described hereinafter, to the method for synthesizing these oligosaccharides or polysaccharides and glycoconjugates, to derivatives of these oligosaccharides or polysaccharides, to compositions containing same, and also to the use of the glycoconjugates for vaccination purposes. Finally, the present invention relates to methods for diagnosing a Shigella flexneri infection using one or more oligosaccharides or polysaccharides or conjugates thereof.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics