74372-90-0

Upstream product

• 40246-26-2 3,4,6-tri-O-benzyl-α-D-glucopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 74372-91-1 2,3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 625-95-6 3-Iodotoluene 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 2873-29-2 D-glucal triacetate 
• 13265-84-4 D-glucal 
• 74372-92-2 (3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-fluoro-tetrahydro-pyran-3-ol 
• 74372-92-2 3,4,6-Tri-O-benzyl-β-D-glucopyranosyl fluoride 

Downstream Products

• 135192-41-5 3,4-dimethylphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 135192-40-4 2,6-dimethylphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 130781-26-9 4-Pentenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 121654-12-4 (1R,2S,5R)-menthyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138925-04-9 2'-bromophenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 135192-33-5 O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzyl-2-deoxy-D-lyxo-hex-1-enitol 
• 130781-25-8 Phenyl 3,4,6-tri-O-benzyl-1-seleno-α-D-glucopyranoside 
• 40246-33-1 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-1:2,3:4-di-O-isopropylidene-α-D-galactopyranoside 
• 20672-67-7 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol 
• 133004-71-4 (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole 
• 135192-39-1 phenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138925-03-8 2'-carbomethoxyphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 1064-10-4 hexaphenylditin 
• 161145-52-4 triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane 

Relevant academic research and scientific papers

Synthesis and Conformational Analysis of 2-O-Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides

Synthesis of orthogonally protected 2-silyl nucleosides were achieved by trans opening of sugar epoxides with nucleobases catalyzed by trimethylsilyltrifluoromethanesulfonate using hexamethyldisilazane both as solvent and silylating agent. Both α and β nu

A Short Sequence for the Iterative Synthesis of Fused Polyethers

A simple and efficient four-step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring-closing metathesis and hydroboration with acidic workup. Cruc

2-: O-Benzyloxycarbonyl protected glycosyl donors: A revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

By reviving an old idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O-2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1,2-trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.

An Isolable and Bench-Stable Epoxidizing Reagent Based on Triazine: Triazox

A new triazine-based oxidizing reagent, 2-hydroperoxy-4,6-diphenyl-1,3,5-triazine (Triazox), has been developed. The reagent can be synthesized from inexpensive starting materials and is a bench-stable solid that is isolable in pure form. Epoxidation of alkenes possessing acid-sensitive functionalities using Triazox proceeded in good to excellent yields. The accompanying nonacidic triazinone coproduct can be easily removed by filtration. These features indicate that Triazox is a practically useful oxidizing reagent.

METHOD FOR PRODUCING GLYCYRRHIZINIC ACID AND GALACTURO GLYCYRRHIZINIC ACID, AND INTERMEDIATE USED FOR THE PRODUCTION METHOD

PROBLEM TO BE SOLVED: To provide a synthesis method that makes it possible to produce high-purity glycyrrhizinic acid or galacturo glycyrrhizinic acid, simply and in high yields. SOLUTION: A production method includes performing glycosylation of position-3 hydroxy group of glycyrrhetinic acid, then performing selective galactosylation or glycosylation at position-2', and through deprotection, performing selective oxidation of a primary hydroxy group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides

Stereoselective manipulations at the C1 anomeric position of saccharides are one of the central goals of preparative carbohydrate chemistry. Historically, the majority of reactions forming a bond with anomeric carbon has focused on reactions of nucleophiles with saccharide donors equipped with a leaving group. Here, we describe a novel approach to stereoselective synthesis of C-aryl glycosides capitalizing on the highly stereospecific reaction of anomeric nucleophiles. First, methods for the preparation of anomeric stannanes have been developed and optimized to afford both anomers of common saccharides in high anomeric selectivities. We established that oligosaccharide stannanes could be prepared from monosaccharide stannanes via O-glycosylation with Schmidt-type donors, glycal epoxides, or under dehydrative conditions with C1 alcohols. Second, we identified a general set of catalytic conditions with Pd2(dba)3 (2.5 mol%) and a bulky ligand (JackiePhos, 10 mol%) controlling the β-elimination pathway. We demonstrated that the glycosyl cross-coupling resulted in consistently high anomeric selectivities for both anomers with mono- and oligosaccharides, deoxysugars, saccharides with free hydroxyl groups, pyranose, and furanose substrates. The versatility of the glycosyl cross-coupling reaction was probed in the total synthesis of salmochelins (siderophores) and commercial anti-diabetic drugs (gliflozins). Combined experimental and computational studies revealed that the β-elimination pathway is suppressed for biphenyl-type ligands due to the shielding of Pd(II) by sterically demanding JackiePhos, whereas smaller ligands, which allow for the formation of a Pd-F complex, predominantly result in a glycal product. Similar steric effects account for the diminished rates of cross-couplings of 1,2-cis C1-stannanes with aryl halides. DFT calculations also revealed that the transmetalation occurs via a cyclic transition state with retention of configuration at the anomeric position. Taken together, facile access to both anomers of various glycoside nucleophiles, a broad reaction scope, and uniformly high transfer of anomeric configuration make the glycosyl cross-coupling reaction a practical tool for the synthesis of bioactive natural products, drug candidates, allowing for late-stage glycodiversification studies with small molecules and biologics.

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O

α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether

The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.

Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups

In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.

Convenient synthesis of 1,3-dithiolane-2-thiones: Cyclic trithiocarbonates as conformational locks

A series of novel 1,3-dithiolane-2-thiones, or cyclic trithiocarbonates, has been prepared by a new simple procedure: a treatment of the corresponding epoxides with the commercially available potassium ethyl xanthogenate, KSC(S)OEt. The stereochemistry of the products was determined by 1H NMR and in some cases by single-crystal X-ray data. Cyclohexane-based 1,3- dithiolane-2-thiones revealed a trans-fusion of the carbo- and hetero-cycles. The products obtained from the mono-substituted cyclohexene oxides demonstrated an axial position of the substituents. Thus the epoxide transformation into trithiocarbonate can be used as a method for locking cyclic compounds in unstable conformations.ARKAT-USA, Inc.