129778-39-8

Upstream product

• 119005-59-3 methyl 4,5,7-tri-O-benzyl-2,3-dideoxy-2-(prop-2-enyl)-β-D-arabino-hept-2-ulopyranosonate 
• 119068-33-6 phenyl 3,4,6-tri-O-benzyl-2-deoxy-1-sulphonyl-αβ-D-arabino-pyranoside 
• 132674-50-1 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose 
• 762-72-1 allyl-trimethyl-silane 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 264881-65-4 3,4,6-tri-O-benzyl-2-deoxy-1-O-acetyl-α/β-D-glucopyranose 

Relevant academic research and scientific papers

C -Glycosylation enabled by N -(glycosyloxy)acetamides

The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.

Gold(i)-catalyzed C-glycosylation of glycosyl: Ortho -alkynylbenzoates: The role of the moisture sequestered by molecular sieves

C-Glycosylation of glycosyl ortho-hexynylbenzoates with allyltrimethylsilane or silyl enol ethers could proceed smoothly under the catalysis of Ph3PAuNTf2 to provide the corresponding C-glycosides in high yields and stereoselectivity, wherein the moisture sequestered by the molecular sieves was disclosed to play a critical role in the gold(i)-catalytic cycle.

Reduction of 2-arylthio -β C-D-glucopyranosides with different functional groups in the lateral chain

2-Arylthio -β C-D-glucopyranosides with a carbonyl or methoxy group in the lateral chain (1 and 2) can be converted to the corresponding 2-deoxy -β C-D-glucopyranosides (1a and 2a) using Raney Ni. Reduction of 2-arylthio -β C-D-glucopyranosides bearing an

Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit

(Chemical Equation Presented) Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (α:β) ratio of diastereomers under SN1-like reaction conditions. Stereoselective formation of the 2-deoxy-α-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stereoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastereomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.

The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ions

The three-dimensional structures of dioxocarbenium ions related to glycosyl cations were determined by an analysis of spectroscopic, computational, and reactivity data. Hypothetical low-energy structures of the dioxocarbenium ions were correlated with both experimentally determined 1H NMR coupling constants and diastereoselectivity results from nucleophilic substitution reactions. This method confirmed the pseudoaxial preference of C-3 alkoxy-substituted systems and revealed the conformational preference of the C-5 alkoxymethyl group. Although the monosubstituted C-5 alkoxymethyl substituent preferred a pseudoequatorial orientation, the C-5-C-6 bond rotation was controlled by an electrostatic effect. The preferred diaxial conformer of the trans-4, 5-disubstituted tetrahydropyranyl system underscored the importance of electrostatic effects in dictating conformational equilibria. In the 2-deoxymannose system, although steric effects influenced the orientation of the C-5 alkoxymethyl substituent, the all-axial conformer was favored because of electrostatic stabilization.

Diastereoselective Free-Radical Reactions. Part 2. Synthesis of 2-Deoxy-β-C-pyranosides by Diastereoselective Hydrogen-Atom Transfer

C-Glycosides of 2,3-dideoxy-arabino-heptulosonate esters are prepared from the corresponding 2,3-dideoxy-1-phenylsulphonyl derivatives by reductive desulphonylation with lithium naphthalenide and quenching of the so-formed enolate with appropriate alkyl h

Synthesis of 2-deoxy-β-C-pyranosides by diastereoselective hydrogen atom transfer

2-Deoxy-β-C-pyranosides are synthesized by sequential treatment of methyl 3-deoxy-2-phenylsulphonyl-4,5,7-tri-O-benzyl-D-arabino-heptulosonate with lithium naphthalenide and an alkyl halide followed by saponification and reductive decar□ylation. (Chemical