92414-08-9

Upstream product

• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 13871-89-1 trimethylsilyl cyclohexyl ether 
• 91110-24-6 Acetic acid (2S,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl ester 
• 108-93-0 cyclohexanol 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 

Relevant academic research and scientific papers

Dehydrative glycosylation with cyclic phosphonium anhydrides

Cyclic phosphonium anhydrides generated from bis-phosphine oxides and trifluoromethanesulfonic anhydride are shown as general coupling reagents in a dehydrative glycosylation reaction of C1-hemiacetals. This reaction protocol is characterized by a broad substrate scope and high yields, including reactions of O-, C-, N-, and S-based nucleophiles with furanose, pyranose, and deoxysugar donors.

α-selective ribofuranosylation of alcohols with ribofuranosyl iodides and triphenylphosphine oxide

Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.

Dehydrative glycosylation of tri-O-benzylated 1-hydroxyribofuranose catalyzed by a copper(II) complex

A phosphine/Cu(II) complex catalyzes the dehydrative glycosylation of tri-O-benzylated 1-hydroxyribofuranose to give the ribofuranoside with high stereoselectivity.

Synthesis of β-D-ribofuranosyl-(1→3)-α-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system

Β-D-Ribofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)- L-rhamnopyranose, the trisaccharide repeating unit of the C. freundii O28, 1c O-specific polysaccharide, was synthesized using in situ activating glycosylation of the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivatives of methyl, allyl, and benzyl α-L-rhamnosides.

A convenient method for the preparation of disaccharides by transglycosylation of methyl glycosides

Transglycosylation of methyl glycosides with various glycosyl acceptors using a Sn(OTf)2-Me3SiCl promoter system in the presence of molecular sieves 5A afforded the corresponding glycosides. Several useful disaccharides are effectively prepared in good yields with moderate to good stereoselectivities.

Trityl salt catalyzed stereoselective glycosylation of alcohols with 1-hydroxyribofuranose

In the presence of a catalytic amount of several trityl salts, 2,3,5-tri-O-benzyl-D-ribofuranose smoothly reacted with alcohols to give various β-ribofuranosides in high yields with high stereoselectivity while reversed stereoselectivity was observed in t

A significant effect of a lithium salt in the stereocontrolled synthesis of α-D-ribofuranosides

Lithium bis[(trifluoromethyl)sulfonyl]imide was found to be a new and effective additive in the stereocontrolled synthesis of α-D-ribofuranosides from 2,3,5-tri-O-benzyl-D-ribofuranose and several alcohols while β-anomers were formed in the absence of the

An efficient glycosylation reaction of 1-hydroxy sugars with various nucleophiles using a catalytic amount of activator and hexamethyldisiloxane

In the presence of hexamethyldisiloxane and anhydrous calcium sulfate, a catalytic amount of activator such as tin(II) trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate, lanthanum trifluoromethanesulfonate or tin(II) chloride smoothly promote

Stereoselective syntheses of α-D- and β-D-ribofuranosides catalyzed by the combined use of silver salts and their partners

α-D-Ribofuranosides are stereoselectively synthesized in high yields from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-D-ribofuranose (1) and trimethylsilylated nucleophiles by the use of silver salts in the coexistence of 3 molar amounts of lithium perchlorate, whi

Catalytic Synthesis of β-D-Ribofuranosides from D-Ribofuranose and Alcohols

Catalytic synthesis of β-D-ribofuranosides from C-1 free ribofuranose, 2,3,5-tri-O-benzyl-D-ribofuranose, and alcohols is efficiently performed by combined use of silver salts and Lawesson's reagent, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-