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.

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

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

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

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

Catalytic Stereoselective Synthesis of α- or β-Ribofuranosides by Combined Use of Silver Salts and Lithium Perchlorate or Diphenyltin Sulfide

Catalytic stereoselective synthesis of 1,2-cis- or 1,2-trans-ribofuranosides from 1-O-iodoacetylribofuranose and alkyl trimethylsilyl ethers is efficiently promoted by combined use of silver salts and lithium perchlorate or diphenyltin sulfide (Ph2Sn=S) u