4163-39-7

Upstream product

• 98-88-4 benzoyl chloride 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 627466-64-2 2,3,4,6-tetra-O-benzoyl-D-glucopyranose 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 4410-31-5 (RS)-mandelamide 
• 151767-11-2 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 125367-09-1 n-pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 
• 123487-55-8 3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 
• 65236-83-1 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 65236-82-0 1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 950602-83-2 4-methylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 
• 1392228-57-7 tolyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside (R)-S-oxide 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 

Downstream Products

• 118579-76-3 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 125135-28-6 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 128503-40-2 methyl-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 128503-39-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

IPy2BF4/HF-pyridine: A new combination of reagents for the transformation of partially unprotected thioglycosides and n-pentenyl glycosides to glycosyl fluorides

(Chemical Equation Presented) The combination of bis(pyridinium)iodonium (I) tetrafluoroborate (IPy2BF4), and hydrogen fluoride pyridine (HF-py) forms an iodine monofluoride (IF) synthetic equivalent that can be used in the preparati

Synthesis and Biological Evaluation of Cyanogenic Glycosides

An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies

n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga's reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2BF4),

Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates

Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.

Reaction of 1,2-orthoesters with HF-pyridine: A method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis

Glycosyl fluorides can be prepared In an efficient manner by treatment of pyranose- or furanose-derlved 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method Is compatible with the presence of a variety of protecting groups, including fert-

IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: A new pair of semiorthogonal glycosyl donors

Bis(pyridinium) iodonium(1) tetrafluoroborate (IPy2BF 4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new

Stereospecific α-D-mannosylation

The stereospecific formation of α-D-mannosyl glycosidic linkages has been achieved in high yield using tetra-O-pivaloyl-α-D-mannopyranosyl fluoride and boron trifluoride diethyl etherate in dichloromethane. Examples of the α-D-mannosylation of primary, secondary, benzylic and phenolic hydroxyl groups are described. Copyright (C) 1999 Elsevier Science Ltd.

THIOGLYCOSIDES AS POTENTIAL GLYCOSYL DONORS IN ELECTROCHEMICAL GLYCOSYLATION REACTIONS. PART 1: THEIR PREPARATION AND REACTIVITY TOWARD SIMPLE ALCOHOLS

Costant potential electrolysis of several glycosyl donors such as substituted phenyl 2,3,4,6-tetra-O-acetyl, benzoyl or benzyl-1-thio-β-D-gluco or galactopyranosides in dry acetonitrile in the presence of various primary, secondary or tertiary alcohols performed in an undivided cell, gave preferentially β-linked saccharides in moderate to good yields according to the nature of the protective groups on the sugar moiety. 2-Deoxy-2-phthalimido-1-thio-β-D-gluco derivatives gave the β-glucosides selectively in excellent yields.It was found, as expected, that substitution of the phenyl group with methoxy or methyl radicals facilitates the electrochemical glycosylation reaction by lowering the oxidation potentials of the corresponding thioglycosides.

A CONVENIENT, ONE-STEP, HIGH-YIELD REPLACEMENT OF AN ANOMERIC HYDROXYL GROUP BY A FLUORINE ATOM USING DAST. PREPARATION OF GLYCOSYL FLUORIDES.

The anomeric hydroxyl group of various furanose and pyranose hemiacetals can be replaced by a fluorine atom stereoselectively, conveniently, mildly, and on gram-scale using DAST in THF at room temperature.