85422-88-4

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 98-86-2 acetophenone 
• 53008-64-3 Toluene-4-sulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 85422-87-3 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one 

Downstream Products

• 81972-20-5 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol 
• 85422-91-9 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 85505-09-5 2,3,4,6-O-tetra-acetyl-1-deoxy-1-(2-phenylethyl)-β-D-glucopyranose 

Relevant academic research and scientific papers

Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation

C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results i

The mukaiyama type aldol reaction for the synthesis of: Trans-2,6-disubstituted tetrahydropyrans: Synthesis of diospongin a and b

An efficient synthesis protocol for the preparation of trans-2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a catalytic amount of molecular iodine. The feature of this novel conversion includes milder reaction conditions, broader substrate scope, functional group tolerance and good diastereoselectivity. The efficiency and practicality of the current method were successfully displayed in the total synthesis of diospongin A and B in good yields.

Epimerization of α- to β-C-Glucopyranosides under Mild Basic Conditions

A number of β-C-glucopyranosides having an activated methylene or methine group bonded to the anomeric carbon are obtainable in quantitative yield from the corresponding α-isomers by simple equilibration catalysed by various bases at room temperature.

O-Glycosyl Imidates, 19. - Reactions of Glycosyl Trichloroacetimidates with Silylated C-Nucleophiles

Reaction of O-benzyl-protected α-glycopyranosyl trichloroacetimidates 1 and the xylo analogues 7 with silyl enol ethers or allyltrimethylsilane as C-nucleophiles yields with zink chloride as catalyst mainly or exclusively α-C-glycosides (5a-α to 5h-α, 8b,